[2-(hydroxymethyl)phenyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 1.2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chromotographed (flash silica gel, 1:1 t-butyl methyl ether: hexanes) to afford the title compound as a white solid. (0.99 g, 49%) The solvent was removed under reduced pressure

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

Procedure: Phthalyl alcohol (1.15 g, 8.31 mmol) was dissolved in 5 ml of THF, and bisdiisopropylaminochlorophosphine (2.21 g, 8.31 mmol) which was dissolved in 5 ml of THF was added dropwise to the solution at -15° C. under a nitrogen atmosphere. Afterward, the temperature of the solution was adjusted to room temperature, and after the disappearance of phthalyl alcohol had been confirmed, hydrochloride of diisopropylamine was washed with ether. The wash liquor was concentrated and then distilled in order to obtain the desired product having a melting point of from 150° to 155° C. (0.7 mmHg). was added dropwise to the solution at -15° C. under a nitrogen atmosphere was adjusted to room temperature hydrochloride of diisopropylamine was washed with ether The wash liquor was concentrated distilled in order

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

Procedure: Phthalyl alcohol (1.15 g, 8.31 mmol) was dissolved in 5 ml of THF, and bisdiisopropylaminochlorophosphine (2.21 g, 8.31 mmol) which was dissolved in 5 ml of THF was added dropwise to the solution at -15° C. under a nitrogen atmosphere. Afterward, the temperature of the solution was adjusted to room temperature, and after the disappearance of phthalyl alcohol had been confirmed, hydrochloride of diisopropylamine was washed with ether. The wash liquor was concentrated and then distilled in order to obtain the desired product having a melting point of from 150° to 155° C. (0.7 mmHg). was added dropwise to the solution at -15° C. under a nitrogen atmosphere was adjusted to room temperature hydrochloride of diisopropylamine was washed with ether The wash liquor was concentrated distilled in order

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer were placed 50 g of o-xylylene glycol, 39.2 g of 60% by weight nitric acid, 197.6 g of water, and 213.2 g of acetic acid. The mixture was raised in temperature to 70° C. on an oil bath and was stirred under these conditions for 2 hours. After cooling, the reaction mixture was analyzed by gas chromatography to find that the raw material o-xylylene glycol was completely absent and that phthalaldehyde was formed in a yield of 60%. In addition, phthalide (yield: 6%) and an ester of the raw material were formed as by-products. The obtained reaction mixture was extracted with two portions of toluene, the organic layer was distilled and thereby yielded phthalaldehyde in a yield of 45% on the basis of o-xylylene glycol. Gas chromatographic analysis revealed that phthalaldehyde had a purity of 95.0%. In addition, phthalide was formed in a yield of 10%. In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer After cooling

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer were placed 13.3 g of o-xylylene glycol, 36.7 g of o-xylylene oxide, 85.1 g of 60% by weight nitric acid, 165.5 g of water, and 199.5 g of acetic acid. The mixture was raised in temperature to 70° C. on an oil bath and was stirred under these conditions for 1 hour. After cooling, the reaction mixture was analyzed by gas chromatography to find that the raw material o-xylylene glycol was completely absent and that phthalaldehyde was formed in a yield of 84%. The obtained reaction mixture was extracted with two portions of toluene, the organic layer was distilled and thereby yielded phthalaldehyde in a yield of 67% on the basis of o-xylylene glycol. Gas chromatographic analysis revealed that phthalaldehyde had a purity of 98.8%. In addition, phthalide was formed in a yield of 11%. In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer After cooling

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer were placed 50 g of o-xylylene glycol, 78.4 g of 60% by weight nitric acid, 170.1 g of water, and 201.5 g of acetic acid. The mixture was raised in temperature to 70° C. on an oil bath and was stirred under these conditions for 1 hour. After cooling, the reaction mixture was analyzed by gas chromatography to find that the raw material o-xylylene glycol was completely absent and that phthalaldehyde was formed in a yield of 84%. The obtained reaction mixture was extracted with two portions of toluene, the organic layer was distilled and thereby yielded phthalaldehyde in a yield of 67% on the basis of o-xylylene glycol. Gas chromatographic analysis revealed that phthalaldehyde had a purity of 98.8%. In addition, phthalide was formed in a yield of 12%. In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer After cooling

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-benzenedimethanol (2.00 g, 14.5 mmol) and triethylamine (8.08 mL, 58.0 mmol) in 50 mL of CH2Cl2 was added thionyl chloride (1.59 mL, 21.7 mmol) dropwise at 0° C. The resulting dark brown solution was stirred at 0° C. for 1 h. Then 30 mL of brine was added. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (20 mL) once. The combined organic layers were dried with Na2SO4 and evaporated. The residue was further dried on vacuum pump for 2 h to afford crude cyclic sulfite (2.48 g. 13.5 mmol). This crude cyclic sulfite was dissolved in a mixture of acetonenitrile, chloroform and water (20, 20, 30 mL respectively). NaIO4 (4.33 g, 20.3 mmol) and RuCl2.xH2O (60 mg) were added at 0° C. The resulting reaction mixture was vigorously stirred at 0° C. for 1 h. 30 mL of brine was added, followed by 60 mL of Et2O. The aqueous layer was extracted with Et2O (30 mL×2). The combined organic layers were dried with Na2SO4 and evaporated. The resulting solid residue was purified by passing through a short silica gel plug (CH2Cl2 as eluent) to give 40 as a white solid (2.55 g, 88%). The organic layer was separated the aqueous layer was extracted with CH2Cl2 (20 mL) once The combined organic layers were dried with Na2SO4 evaporated The residue was further dried on vacuum pump for 2 h to afford crude cyclic sulfite (2.48 g. 13.5 mmol) xH2O (60 mg) were added at 0° C The resulting reaction mixture was vigorously stirred at 0° C. for 1 h The aqueous layer was extracted with Et2O (30 mL×2) The combined organic layers were dried with Na2SO4 evaporated The resulting solid residue was purified

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reagent, α,α′-dihydroxy-o-xylene, produced by Aldrich Co. (69.5 g, 0.5 mol) was placed in a 500-mL four-neck flask equipped with a condenser tube, a stirring blade, a thermometer, and a dropping funnel, and 35% hydrochloric acid (100 g, 1.0 mol) was added thereto. The mixture was stirred at 70° C. for one hour. After completion of reaction, the reaction mixture was allowed to stand, so that two-separated layers were formed. The reaction was analyzed through GC while stirring again during sampling. From the obtained concentration of α-chloro-α′-hydroxy-o-xylene, the yield of α-chloro-α′-hydroxy-o-xylene was calculated to be 91% based on α,α′-dihydroxy-o-xylene. The conversion of α,α′-dihydroxy-o-xylene was 99%, and α,α′-dichloro-o-xylene (5%) and phthalan (2%) were formed as by-products. (69.5 g, 0.5 mol) was placed in a 500-mL four-neck flask equipped with a condenser tube After completion of reaction so that two-separated layers were formed while stirring again during sampling

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

Procedure: The procedure of Example 15 was performed except that the pH of the reaction mixture was regulated to 12 by use of sodium hydroxide. The reaction mixture was sampled for analysis. Formation of α,α′-dihydroxy-o-xylene was not observed. Instead, phthalan was formed at a yield of 96% based on α,α′-dichloro-o-xylene. The reaction mixture was sampled for analysis