4-[2-(4-hydroxyphenyl)prop-1-enyl]phenol

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (188.22 grams, 2.0 moles) and chloroacetone (102.81 grams, 1.0 mole as chloroacetone) are added to a reactor and cooled to -10° C. with stirring. The chloroacetone used is a technical grade containing 90% chloroacetone, 2.5% acetone, 6.5% 1,1-dichloroacetone and 1.0% 1,3-dichloroacetone. Concentrated sulfuric acid (98.08 grams, 1.0 mole) is added dropwise to the stirred solution over a one hour period and so as to maintain the reaction temperature between -10° and -11° C. After two hours of post reaction at the -10° C. temperature, the viscous orange oil product is mixed with 500 milliliters of iced deionized water. The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water. After separation, the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol and stirred to provide a solution. Deionized water (250 milliliters) is added to the stirred solution and heating commenced. As the temperature of the mixture increased, the stirred mixture began to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs. At this time, heating and stirring ceases and the mixture is chilled to 5° C. and held therein for 12 hours. The crystalline product is recovered by filtration, washed with two 150 milliliter portions of deionized water, then dried at 90° C. and 5 mm Hg to a constant weight of 103 grams. Nuclear magnetic resonance spectroscopy and infrared spectrophotometric analysis confirmed the product structure. so as to maintain the reaction temperature between -10° and -11° C After two hours of post reaction at the -10° C. temperature The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water After separation the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol stirred to provide a solution heating As the temperature of the mixture increased heating reaches 90° C. a massive precipitation of white crystalline plates At this time, heating stirring ceases the mixture is chilled to 5° C. The crystalline product is recovered by filtration washed with two 150 milliliter portions of deionized water dried at 90° C.

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4'-Dihydroxy-alpha-methylstilbene (152.73 grams, 1.35 hydroxyl equivalents) from A above, epichlorohydrin (624.58 grams, 6.75 moles), deionized water (54.31 grams, 8.0 percent by weight of the epichlorohyrin used) and isopropanol (336.31 grams, 35 percent by weight of the epichlorohydrin used) is added to a reactor and heated to 55° C. with stirring under a nitrogen atmosphere. Once the 55° C. reaction temperature is achieved, sodium hydroxide (48.6 grams, 1.22 moles) dissolves in deionized water (194.4 grams) is added dropwise to the reactor over a 45 minute period so as to maintain reaction temperature between 55° and 59° C. Ten minutes after completion of the aqueous sodium hydroxide addition, the stirring is stopped and the aqueous layer which separated from the reaction mixture is pipetted off and discarded. Stirring is resumed and after a total of twenty minutes following completion of the initial aqueous sodium hydroxide addition, a second solution of sodium hydroxide (21.6 grams, 0.54 mole) dissolved in deionized water (86.4 grams) is added to the reactor over a twenty minute period so as to maintain the 55° C. reaction temperature. Fifteen minutes after completion of the aqueous sodium hydroxide addition, the recovered reaction mixture is added to a separatory funnel and washed with 750 milliliters of deionized water. The separated organic layer is washed a second time (750 milliliters deionized water), recovered and then rotary evaporated under vacuum for 45 minutes at 110° C. then 30 minutes at 130° C. The product is recovered (218.6 grams) as a crystalline solid with an epoxide equivalent weight of 183.33. is added to a reactor Once the 55° C. reaction temperature is added dropwise to the reactor over a 45 minute period so as to maintain reaction temperature between 55° and 59° C the aqueous layer which separated from the reaction mixture Stirring after a total of twenty minutes completion of the initial aqueous sodium hydroxide addition is added to the reactor over a twenty minute period so as to maintain the 55° C. reaction temperature the recovered reaction mixture is added to a separatory funnel washed with 750 milliliters of deionized water The separated organic layer is washed a second time (750 milliliters deionized water) recovered rotary evaporated under vacuum for 45 minutes at 110° C. 30 minutes at 130° C The product is recovered (218.6 grams) as a crystalline solid with an epoxide equivalent weight of 183.33

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (188.22 grams, 2.0 moles) and chloroacetone (102.81 grams. 1.0 mole as chloroacetone) are added to a reactor and cooled to -10° C. with stirring. The chloroacetone used is a technical grade containing 90% chloroacetone. 2.5% acetone, 6.5% 1,1-dichoroacetone and 1.0% 1,3-dichloroacetone. Concentrated sulfuric acid (98.08 grams, 1.0 mole) is added dropwise to the stirred solution over a one hour period in order to maintain the reaction temperature between -10° C. and -11° C. After two hours of post reaction at the -10° C. temperature, the viscous orange oil product is mixed with 500 milliliters of iced deionized water. The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water. After separation, the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol and stirred to provide a solution. Deionized water (250 milliliters) is added to the stirred solution and heating commenced. As the temperature of the mixture increases, the stirred mixture begins to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs. At this time, heating and stirring ceases and the mixture is chilled to 5° C. and held therein for 12 hours. The crystalline product is recovered by filtration, washed with two 150 milliliter portions of deionized water, then dried at 90° C. and 5 mm Hg to a constant weight of 103 grams. Nuclear magnetic resonance spectroscopy and infrared spectrophotometric analysis confirms the product structure for 4,4'-dihydroxy-α-methylstilbene. to maintain the reaction temperature between -10° C. and -11° C After two hours of post reaction at the -10° C. temperature The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water After separation the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol stirred to provide a solution heating As the temperature of the mixture increases heating reaches 90° C. a massive precipitation of white crystalline plates At this time, heating stirring ceases the mixture is chilled to 5° C. The crystalline product is recovered by filtration washed with two 150 milliliter portions of deionized water dried at 90° C.

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4'-Dihydroxy-alpha-methylstilbene 152.73 grams, 1.35 hydroxyl equivalents) from A above, epichlorohydrin (624.58 grams, 6.75 moles), deionized water (54.31 grams, 8.0 percent by weight of the epichlorohyrin used) and isopropanol (336.31 grams, 35 percent by weight of the epichlorohydrin used) is added to a reactor and heated to 55° C. with stirring under a nitrogen atmosphere. Once the 55° C. reaction temperature is achieved, sodium hydroxide (48.6 grams, 1.22 moles) dissolves in deionized water (194.4 grams) is added dropwise to the reactor over a 45 minute period so as to maintain reaction temperature between 55° and 59° C. Ten minutes after completion of the aqueous sodium hydroxide addition, the stirring is stopped and the aqueous layer which separated from the reaction mixture is pipetted off and discarded. Stirring is resumed and after a total of twenty minutes following completion of the initial aqueous sodium hydroxide addition, a second solution of sodium hydroxide (21.6 grams, 0.54 mole) dissolved in deionized water (86.4 grams) is added to the reactor over a twenty minute period 30 as to maintain the 55° C. reaction temperature. Fifteen minutes after completion of the aqueous sodium hydroxide addition, the recovered reaction mixture is added to a separatory funnel and washed with 750 milliliters of deionized water. The separated organic layer is washed a second time (750 milliliters deionized water), recovered and then rotary evaporated under vacuum for 45 minutes at 110° C. then 30 minutes at 130° C. The product is recovered (218.6 grams) as a crystalline solid with an epoxide equivalent weight of 183.33. is added to a reactor Once the 55° C. reaction temperature is added dropwise to the reactor over a 45 minute period so as to maintain reaction temperature between 55° and 59° C the aqueous layer which separated from the reaction mixture Stirring after a total of twenty minutes completion of the initial aqueous sodium hydroxide addition is added to the reactor over a twenty minute period 30 as to maintain the 55° C. reaction temperature the recovered reaction mixture is added to a separatory funnel washed with 750 milliliters of deionized water The separated organic layer is washed a second time (750 milliliters deionized water) recovered rotary evaporated under vacuum for 45 minutes at 110° C. 30 minutes at 130° C The product is recovered (218.6 grams) as a crystalline solid with an epoxide equivalent weight of 183.33

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (188.22 grams, 2.0 moles) and chloroacetone (102.81 grams. 1.0 mole as chloroacetone) are added to a reactor and cooled to -10° C. with stirring. The chloroacetone used is a technical grade containing 90% chloroacetone, 2.5% acetone, 6.5% 1,1-dichloroacetone and 1.0% 1,3-dichloroacetone. concentrated sulfuric acid (98.08 grams, 1.0 mole) is added dropwise to the stirred solution over a one hour period in order to maintain the reaction temperature between -10° C. and -11° C. After two hours of post reaction at the -10° C. temperature, the viscous orange oil product is mixed with 500 milliliters of iced deionized water. The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water. After separation, the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol and stirred to provide a solution. Deionized water (250 milliliters) is added to the stirred solution and heating commenced. As the temperature of the mixture increases, the stirred mixture begins to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs. At this time, heating and stirring ceases and the mixture is chilled to 5° C. and held therein for 12 hours. The crystalline product is recovered by filtration, washed with two 150 milliliter portions of deionized water, then dried at 90° C. and 5 mm Hg to a constant weight of 103 grams. Nuclear magnetic resonance spectroscopy and infrared spectrophotometric analysis confirms the product structure for 4,4'-dihydroxy-α-methylstilbene. to maintain the reaction temperature between -10° C. and -11° C After two hours of post reaction at the -10° C. temperature The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water After separation the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol stirred to provide a solution heating As the temperature of the mixture increases heating reaches 90° C. a massive precipitation of white crystalline plates At this time, heating stirring ceases the mixture is chilled to 5° C. The crystalline product is recovered by filtration washed with two 150 milliliter portions of deionized water dried at 90° C.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (752.8 grams, 8.0 moles), chloroacetone (384.7 grams, 4.0 moles as chloroacetone) and methylene chloride (600 grams) are added to a reactor and cooled to -10° C. with stirring under a nitrogen atmosphere. The chloroacetone used is a commercial grade containing 96.25% chloroacetone, 0.05% acetone, 3.05% 1,1-dichloroacetone and 0.60% mesityl oxide. Concentrated sulfuric acid (392.32 grams, 4.0 mole) is added dropwise to the stirred solution over a forty five minute period and so as to maintain the reaction temperature between -11° and -9° C. After 150 minutes of post reaction at -11° to -9° C., the viscous, orange colored oil product is mixed with iced deionized water (1000 milliliters). The oil product is separated then washed with a second portion (1000 milliliters) and then a third portion (1000 milliliters) of deionized water. After separation, the recovered oil product is added to a pair of 2 liter beakers along with ethanol (250 milliliters) and stirred to provide solutions. Deionized water (250 milliliters) is added to the stirred solutions and heating commences. As the temperature of the mixture increases, the stirred mixtures began to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs and is followed by immediate coalesence of the precipitated product to an oil. The oil layer is recovered by decantation of the water layer and ethanol (250 milliliters) is added. Deionized water is again added to the stirred solutions as heating commences, in an amount sufficient to induce cloudiness each time clearing is observed. Once the temperature reaches 70° C., a massive precipitation of white crystalline plates again occurs. At this time, stirring is stopped, sufficient deionized water is added to fill both of the beakers and the crystalline slurries are chilled to 4° C. and held therein for 16 hours. The crystalline product is recovered by filtration of the chilled crystalline slurries, added to a beaker along with deionized water (1000 milliliters), then stirred with heating to 100° C. After maintaining the stirred slurry at 100° C. for thirty minutes, the crystalline product is recovered by filtration then again combined with deionized water (1000 milliliters) and stirred with heating to 100° C. The crystalline product is recovered by filtration then dried in a vacuum oven at 100° C. and 5 mm Hg to a constant weight of 478.8 grams. Proton magnetic resonance spectroscopy and Fourier transform infrared spectrophotometric analysis confirms the product structure. so as to maintain the reaction temperature between -11° and -9° C After 150 minutes of post reaction at -11° to -9° C. The oil product is separated then washed with a second portion (1000 milliliters) After separation the recovered oil product is added to a pair of 2 liter beakers along with ethanol (250 milliliters) stirred to provide solutions heating commences As the temperature of the mixture increases heating reaches 90° C. a massive precipitation of white crystalline plates The oil layer is recovered by decantation of the water layer and ethanol (250 milliliters) is added Deionized water is again added to the stirred solutions as heating commences reaches 70° C. a massive precipitation of white crystalline plates At this time, stirring sufficient deionized water is added the crystalline slurries are chilled to 4° C. The crystalline product is recovered by filtration of the chilled crystalline slurries added to a beaker along with deionized water (1000 milliliters) stirred with heating to 100° C After maintaining the stirred slurry at 100° C. for thirty minutes the crystalline product is recovered by filtration stirred with heating to 100° C The crystalline product is recovered by filtration then dried in a vacuum oven at 100° C.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (188.22 grams, 2.0 moles) and chloroacetone (102.81 grams, 1.0 mole as chloroacetone) are added to a reactor and cooled to -10° C. with stirring. The chloroacetone used is a technical grade containing 90% chloroacetone, 2.5% acetone, 6.5% 1,1-dichloroacetone and 1.0% 1,3-dichloroacetone. Concentrated sulfuric acid (98.08 grams, 1.0 mole) is added dropwise to the stirred solution over a one hour period in order to maintain the reaction temperature between -10° C. and -11° C. After two hours of post reaction at the -10° C. temperature, the viscous orange oil product is mixed with 500 milliliters of iced deionized water. The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water. After separation, the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol and stirred to provide a solution. Deionized water (250 milliliters) is added to the stirred solution and heating commenced. As the temperature of the mixture increases, the stirred mixture begins to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs. At this time, heating and stirring ceases and the mixture is chilled to 5° C. and held therein for 12 hours. The crystalline product is recovered by filtration, washed with two 150 milliliter portions of deionized water, then dried at 90° C. and 5 mm Hg to a constant weight of 103 grams. Nuclear magnetic resonance spectroscopy and infrared spectrophotometric analysis confirms the product structure for 4,4'-dihydroxy-α-methylstilbene. to maintain the reaction temperature between -10° C. and -11° C After two hours of post reaction at the -10° C. temperature The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water After separation the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol stirred to provide a solution heating As the temperature of the mixture increases heating Once the temperature reaches 90° C. a massive precipitation of white crystalline plates At this time, heating stirring ceases the mixture is chilled to 5° C. The crystalline product is recovered by filtration washed with two 150 milliliter portions of deionized water dried at 90° C.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (188.22 grams, 2.0 moles) and chloroacetone (102.81 grams, 1.0 mole as chloroacetone) are added to a reactor and cooled to -10° C. with stirring. The chloroacetone used is a technical grade containing 90% chloroacetone, 2.5% acetone, 6.5% 1,1-dichloroacetone and 1.0% 1,3-dichloroacetone. Concentrated sulfuric acid (98.08 grams, 1.0 mole) is added dropwise to the stirred solution over a one hour period in order to maintain the reaction temperature between -10° C. and -11° C. After two hours of post reaction at the -10° C. temperature, the viscous orange oil product is mixed with 500 milliliters of iced deionized water. The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water. After separation, the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol and stirred to provide a solution. Deionized water (250 milliliters) is added to the stirred solution and heating commenced. As the temperature of the mixture increases, the stirred mixture begins to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs. At this time, heating and stirring ceases and the mixture is chilled to 5° C. and held therein for 12 hours. The crystalline product is recovered by filtration, washed with two 150 milliliter portions of deionized water, then dried at 90° C. and 5 mm Hg to a constant weight of 103 grams. Nuclear magnetic resonance spectroscopy and infrared spectrophotometric analysis confirms the product structure for 4,4'-dihydroxy-α-methylstilbene. to maintain the reaction temperature between -10° C. and -11° C After two hours of post reaction at the -10° C. temperature The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water After separation the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol stirred to provide a solution heating As the temperature of the mixture increases heating Once the temperature reaches 90° C. a massive precipitation of white crystalline plates At this time, heating stirring ceases the mixture is chilled to 5° C. The crystalline product is recovered by filtration washed with two 150 milliliter portions of deionized water dried at 90° C.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (188.22 grams, 2.0 moles) and chloroacetone (102.81 grams, 1.0 mole as chloroacetone) are added to a reactor and cooled to -10° C. with stirring. The chloroacetone used is a technical grade containing 90% chloroacetone, 2.5% acetone, 6.5% 1,1-dichloroacetone and 1.0% 1.3-dichloroacetone. Concentrated sulfuric acid (98.08 grams, 1.0 mole) is added dropwise to the stirred solution over a one hour period in order to maintain the reaction temperature between -10° C. and -11° C. After two hours of post reaction at the -10° C. temperature, the viscous orange oil product is mixed with 500 milliliters of iced deionized water. The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water. After separation, the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol and stirred to provide a solution. Deionized water (250 milliliters) is added to the stirred solution and heating commenced. As the temperature of the mixture increases, the stirred mixture begins to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs. At this time, heating and stirring ceases and the mixture is chilled to 5° C. and held therein for 12 hours. The crystalline product is recovered by filtration, washed with two 150 milliliter portions of deionized water, then dried at 90° C. and 5 mm Hg to a constant weight of 103 grams. Nuclear magnetic resonance spectroscopy and infrared spectrophotometric analysis confirms the product structure for 4,4'-dihydroxy-α-methylstilbene. to maintain the reaction temperature between -10° C. and -11° C After two hours of post reaction at the -10° C. temperature The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water After separation the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol stirred to provide a solution heating As the temperature of the mixture increases heating reaches 90° C. a massive precipitation of white crystalline plates At this time, heating stirring ceases the mixture is chilled to 5° C. The crystalline product is recovered by filtration washed with two 150 milliliter portions of deionized water dried at 90° C.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (188.22 grams, 2.0 moles) and chloroacetone (102.81 grams, 1.0 mole as chloroacetone) are added to a reactor and cooled to -10° C. with stirring. The chloroacetone used is a technical grade containing 90% chloroacetone, 2.5% acetone, 6.5% 1,1-dichloroacetone and 1.0% 1.3-dichloroacetone. Concentrated sulfuric acid (98.08 grams, 1.0 mole) is added dropwise to the stirred solution over a one hour period in order to maintain the reaction temperature between -10° C. and -11° C. After two hours of post reaction at the -10° C. temperature, the viscous orange oil product is mixed with 500 milliliters of iced deionized water. The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water. After separation, the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol and stirred to provide a solution. Deionized water (250 milliliters) is added to the stirred solution and heating commenced. As the temperature of the mixture increases, the stirred mixture begins to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs. At this time, heating and stirring ceases and the mixture is chilled to 5° C. and held therein for 12 hours. The crystalline product is recovered by filtration, washed with two 150 milliliter portions of deionized water, then dried at 90° C. and 5 mm Hg to a constant weight of 103 grams. Nuclear magnetic resonance spectroscopy and infrared spectrophotometric analysis confirms the product structure for 4,4'-dihydroxy-α-methylstilbene. to maintain the reaction temperature between -10° C. and -11° C After two hours of post reaction at the -10° C. temperature The oil product is separated then washed with a second 500 milliliter portion of chilled deionized water After separation the recovered oil product is added to a 2-liter beaker along with 250 milliliters of ethanol stirred to provide a solution heating As the temperature of the mixture increases heating reaches 90° C. a massive precipitation of white crystalline plates At this time, heating stirring ceases the mixture is chilled to 5° C. The crystalline product is recovered by filtration washed with two 150 milliliter portions of deionized water dried at 90° C.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (752.8 grams, 8.0 moles), chloroacetone (384.7 grams, 4.0 moles as chloroacetone) and methylene chloride (600 grams) are added to a reactor and cooled to -10° C. with stirring under a nitrogen atmosphere. The chloroacetone used is a commercial grade containing 96.25% chloroacetone, 0.05% acetone, 3.05% 1,1-dichloroacetone and 0.60% mesityl oxide. Concentrated sulfuric acid (392.32 grams, 4.0 mole) is added dropwise to the stirred solution over a forty five minute period and so as to maintain the reaction temperature between -11° and -9° C. After 150 minutes of post reaction at -11° to -9° C., the viscous, orange colored oil product is mixed with iced deionized water (1000 milliliters). The oil product is separated then washed with a second portion (1000 milliliters) and then a third portion (1000 milliliters) of deionized water. After separation, the recovered oil product is added to a pair of 2 liter beakers along with ethanol (250 milliliters) and stirred to provide solutions. Deionized water (250 milliliters) is added to the stirred solutions and heating commences. As the temperature of the mixture increases, the stirred mixtures began to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs and is followed by immediate coalesence of the precipitated product to an oil. The oil layer is recovered by decantation of the water layer and ethanol (250 milliliters) is added. Deionized water is again added to the stirred solutions as heating commences, in an amount sufficient to induce cloudiness each time clearing is observed. Once the temperature reaches 70° C., a massive precipitation of white crystalline plates again occurs. At this time, stirring is stopped, sufficient deionized water is added to fill both of the beakers and the crystalline slurries are chilled to 4° C. and held therein for 16 hours. The crystalline product is recovered by filtration of the chilled crystalline slurries, added to a beaker along with deionized water (1000 milliliters), then stirred with heating to 100° C. After maintaining the stirred slurry at 100° C. for thirty minutes, the crystalline product is recovered by filtration then again combined with deionized water (1000 milliliters) and stirred with heating to 100° C. The crystalline product is recovered by filtration then dried in a vacuum oven at 100° C. and 5 mm Hg to a constant weight of 478.8 grams. Proton magnetic resonance spectroscopy and Fourier transform infrared spectrophotometric analysis confirms the product structure. so as to maintain the reaction temperature between -11° and -9° C After 150 minutes of post reaction at -11° to -9° C. The oil product is separated then washed with a second portion (1000 milliliters) After separation the recovered oil product is added to a pair of 2 liter beakers along with ethanol (250 milliliters) stirred to provide solutions heating commences As the temperature of the mixture increases heating reaches 90° C. a massive precipitation of white crystalline plates The oil layer is recovered by decantation of the water layer and ethanol (250 milliliters) is added Deionized water is again added to the stirred solutions as heating commences reaches 70° C. a massive precipitation of white crystalline plates At this time, stirring sufficient deionized water is added the crystalline slurries are chilled to 4° C. The crystalline product is recovered by filtration of the chilled crystalline slurries added to a beaker along with deionized water (1000 milliliters) stirred with heating to 100° C After maintaining the stirred slurry at 100° C. for thirty minutes the crystalline product is recovered by filtration stirred with heating to 100° C The crystalline product is recovered by filtration then dried in a vacuum oven at 100° C.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (752.8 grams, 8.0 moles), chloroacetone (384.7 grams, 4.0 moles as chloroacetone) and methylene chloride (600 grams) are added to a reactor and cooled to -10° C. with stirring under a nitrogen atmosphere. The chloroacetone used is a commercial grade containing 96.25% chloroacetone, 0.05% acetone, 3.05% 1,1-dichloroacetone and 0.60% mesityl oxide. Concentrated sulfuric acid (392.32 grams, 4.0 mole) is added dropwise to the stirred solution over a forty five minute period and so as to maintain the reaction temperature between -11° and -9° C. After 150 minutes of post reaction at -11° to -9° C., the viscous, orange colored oil product is mixed with iced deionized water (1000 milliliters). The oil product is separated then washed with a second portion (1000 milliliters) and then a third portion (1000 milliliters) of deionized water. After separation, the recovered oil product is added to a pair of 2 liter beakers along with ethanol (250 milliliters) and stirred to provide solutions. Deionized water (250 milliliters) is added to the stirred solutions and heating commences. As the temperature of the mixture increases, the stirred mixtures began to clear. Each time clearing is observed, sufficient deionized water is added to induce cloudiness, followed by continuation of the mixing and heating. Once the temperature reaches 90° C., a massive precipitation of white crystalline plates occurs and is followed by immediate coalesence of the precipitated product to an oil. The oil layer is recovered by decantation of the water layer and ethanol (250 milliliters) is added. Deionized water is again added to the stirred solutions as heating commences, in an amount sufficient to induce cloudiness each time clearing is observed. Once the temperature reaches 70° C., a massive precipitation of white crystalline plates again occurs. At this time, stirring is stopped, sufficient deionized water is added to fill both of the beakers and the crystalline slurries are chilled to 4° C. and held therein for 16 hours. The crystalline product is recovered by filtration of the chilled crystalline slurries, added to a beaker along with deionized water (1000 milliliters), then stirred with heating to 100° C. After maintaining the stirred slurry at 100° C. for thirty minutes, the crystalline product is recovered by filtration then again combined with deionized water (1000 milliliters) and stirred with heating to 100° C. The crystalline product is recovered by filtration then dried in a vacuum oven at 100° C. and 5 mm Hg to a constant weight of 478.8 grams. Proton magnetic resonance spectroscopy and Fourier transform infrared spectrophotometric analysis confirms the product structure. so as to maintain the reaction temperature between -11° and -9° C After 150 minutes of post reaction at -11° to -9° C. The oil product is separated then washed with a second portion (1000 milliliters) After separation the recovered oil product is added to a pair of 2 liter beakers along with ethanol (250 milliliters) stirred to provide solutions heating commences As the temperature of the mixture increases heating reaches 90° C. a massive precipitation of white crystalline plates The oil layer is recovered by decantation of the water layer and ethanol (250 milliliters) is added Deionized water is again added to the stirred solutions as heating commences reaches 70° C. a massive precipitation of white crystalline plates At this time, stirring sufficient deionized water is added the crystalline slurries are chilled to 4° C. The crystalline product is recovered by filtration of the chilled crystalline slurries added to a beaker along with deionized water (1000 milliliters) stirred with heating to 100° C After maintaining the stirred slurry at 100° C. for thirty minutes the crystalline product is recovered by filtration stirred with heating to 100° C The crystalline product is recovered by filtration then dried in a vacuum oven at 100° C.