2-(4-octylphenyl)ethanol

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-octylphenyl)ethanol (5) (46.9 g) is added within 10 min to an aqueous solution containing 3.05 g Na2SO3, 252.9 g 48% HBr and 3.2 g tricaprylmethylammonium chloride. The reaction mixture is heated to 100° C. for 18 to 22 hours with stirring. The resulting 2-phase mixture is cooled to room temperature, diluted with toluene (150 ml) and the aqueous phase is then removed. The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution. The organic phase is treated with basic aluminium oxide, then filtered. The filter residue is washed with toluene (50 ml) and evaporated to yield compound (19) as a clear pale yellow oil. The resulting Compound (19) has the same physico-chemical characteristics as indicated in Example 14. The resulting 2-phase mixture is cooled to room temperature the aqueous phase is then removed The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution The organic phase is treated with basic aluminium oxide filtered The filter residue is washed with toluene (50 ml) evaporated

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

Procedure: Diethyl acetamidomalonate (3.327 g) and 1.137 g of sodium ethylate were dissolved in 50 ml of dry ethanol and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. A solution of 4.000 g of the compound of (3) above in 30 ml of dry ethanol was added thereto and the mixture was refluxed for 15 hours. Methanol (50 ml) was added to the reaction mixture and the insoluble matters were removed. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography to give 3.236 g of diethyl 2-acetamido-2-(2-pentadecynyl)malonate. the mixture was refluxed for 15 hours the insoluble matters were removed The solvent was distilled away under reduced pressure the residue was purified by silica gel column chromatography

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

Procedure: Diethyl acetamidomalonate (3.327 g) and 1.137 g of sodium ethylate were dissolved in 50 ml of dry ethanol and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. A solution of 4.000 g of the compound of (3) above in 30 ml of dry ethanol was added thereto and the mixture was refluxed for 15 hours. Methanol (50 ml) was added to the reaction mixture and the insoluble matters were removed. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography to give 3.236 g of diethyl 2-acetamido-2-(2-pentadecynyl)malonate. melting point=43.0-43.5° C. the mixture was refluxed for 15 hours the insoluble matters were removed The solvent was distilled away under reduced pressure the residue was purified by silica gel column chromatography

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

Procedure: Diethyl acetamidomalonate (3.327 g) and 1.137 g of sodium ethylate were dissolved in 50 ml of dry ethanol and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. A solution of 4.000 g of the compound of (3) above in 30 ml of dry ethanol was added thereto and the mixture was refluxed for 15 hours. Methanol (50 ml) was added to the reaction mixture and the insoluble matters were removed. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography to give 3.236 g of diethyl 2-acetamido-2-(2-pentadecynyl)malonate. melting point=43.0-43.5° C. the mixture was refluxed for 15 hours the insoluble matters were removed The solvent was distilled away under reduced pressure the residue was purified by silica gel column chromatography

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-octylphenyl)ethanol (5) (46.9 g) is added within 10 min to an aqueous solution containing 3.05 g Na2SO3, 252.9 g 48% HBr and 3.2 g tricaprylmethylammonium chloride. The reaction mixture is heated to 100° C. for 18 to 22 hours with stirring. The resulting 2-phase mixture is cooled to room temperature, diluted with toluene (150 ml) and the aqueous phase is then removed. The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution. The organic phase is treated with basic aluminium oxide, then filtered. The filter residue is washed with toluene (50 ml) and evaporated to yield compound (19) as a clear pale yellow oil. The resulting Compound (19) has the same physico-chemical characteristics as indicated in Example 14. The resulting 2-phase mixture is cooled to room temperature the aqueous phase is then removed The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution The organic phase is treated with basic aluminium oxide filtered The filter residue is washed with toluene (50 ml) evaporated

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-octylphenyl)ethanol (5) (46.9 g) is added within 10 min to an aqueous solution containing 3.05 g Na2SO3, 252.9 g 48% HBr and 3.2 g tricaprylmethylammonium chloride. The reaction mixture is heated to 100° C. for 18 to 22 hours with stirring. The resulting 2-phase mixture is cooled to room temperature, diluted with toluene (150 ml) and the aqueous phase is then removed. The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution. The organic phase is treated with basic aluminium oxide, then filtered. The filter residue is washed with toluene (50 ml) and evaporated to yield compound (19) as a clear pale yellow oil. The resulting Compound (19) has the same physico-chemical characteristics as indicated in Example 14. The resulting 2-phase mixture is cooled to room temperature the aqueous phase is then removed The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution The organic phase is treated with basic aluminium oxide filtered The filter residue is washed with toluene (50 ml) evaporated

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-octylphenyl)ethanol (5) (46.9 g) is added within 10 min to an aqueous solution containing 3.05 g Na2SO3, 252.9 g 48% HBr and 3.2 g tricaprylmethylammonium chloride. The reaction mixture is heated to 100° C. for 18 to 22 hours with stirring. The resulting 2-phase mixture is cooled to room temperature, diluted with toluene (150 ml) and the aqueous phase is then removed. The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution. The organic phase is treated with basic aluminium oxide, then filtered. The filter residue is washed with toluene (50 ml) and evaporated to yield compound (19) as a clear pale yellow oil. The resulting Compound (19) has the same physico-chemical characteristics as indicated in Example 14. The resulting 2-phase mixture is cooled to room temperature the aqueous phase is then removed The organic phase is washed twice with a volume of 100 ml of a 9% NaHCO3 solution The organic phase is treated with basic aluminium oxide filtered The filter residue is washed with toluene (50 ml) evaporated

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

Procedure: 2-(4-Octylphenyl)ethanol (53 g) and dichloromethane (500 mL) are charged into a 1 liter three-neck round bottom flask equipped with guard tube and addition funnel. Triethylamine (83.5 g) is added, the mixture is stirred for 30 minutes, then it is cooled to 0° C. Methanesulphonyl chloride (35.2 mL) is added drop-wise at 0° C. and the mass is stirred for 3 hours at room temperature. The mass is diluted with water (700 mL) and the organic layer is separated and the aqueous layer is extracted with dichloromethane (2×250 mL). The combined organic layers is washed with saturated sodium bicarbonate (500 mL) and brine solution (500 mL). The organic layer is separated, dried with sodium sulphate, and concentrated under vacuum to obtain the title compound. Yield: 70 g. equipped with guard tube and addition funnel the mass is stirred for 3 hours at room temperature the organic layer is separated the aqueous layer is extracted with dichloromethane (2×250 mL) The combined organic layers is washed with saturated sodium bicarbonate (500 mL) and brine solution (500 mL) The organic layer is separated dried with sodium sulphate concentrated under vacuum

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

Procedure: Sodium methoxide (22.6 g) and methanol (450 mL) are charged into a 1 liter single neck round bottom flask equipped with a guard tube and stirred for few minutes to form a clear solution. A mixture of 4-octylphenethyl acetate (58 g) and methanol (50 mL) is added and the mass is stirred for 3 hours at room temperature. Methanol is evaporated and the residue is diluted with water (300 mL) and extracted with ethyl acetate (2×300 mL). The extracts are combined, dried with sodium sulphate and concentrated under vacuum to give crude as yellow color liquid. The crude is purified is by a silica gel column using 30% ethyl acetate/hexane as the eluent to yield the title compound. Yield: 56 g. equipped with a guard tube to form a clear solution is added the mass is stirred for 3 hours at room temperature Methanol is evaporated the residue is diluted with water (300 mL) extracted with ethyl acetate (2×300 mL) dried with sodium sulphate concentrated under vacuum to give crude as yellow color liquid The crude is purified

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

Procedure: Diethyl acetamidomalonate (3.327 g) and 1.137 g of sodium ethylate were dissolved in 50 ml of dry ethanol and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. A solution of 4.000 g of the compound of (3) above in 30 ml of dry ethanol was added thereto and the mixture was refluxed for 15 hours. Methanol (50 ml) was added to the reaction mixture and the insoluble matters were removed. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography to give 3.236 g of diethyl 2-acetamido-2-(2-pentadecynyl)malonate. the mixture was refluxed for 15 hours the insoluble matters were removed The solvent was distilled away under reduced pressure the residue was purified by silica gel column chromatography

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

Procedure: Diethyl acetamidomalonate (3.327 g) and 1.137 g of sodium ethylate were dissolved in 50 ml of dry ethanol and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. A solution of 4.000 g of the compound of (3) above in 30 ml of dry ethanol was added thereto and the mixture was refluxed for 15 hours. Methanol (50 ml) was added to the reaction mixture and the insoluble matters were removed. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography to give 3.236 g of diethyl 2-acetamido-2-(2-pentadecynyl)malonate. the mixture was refluxed for 15 hours the insoluble matters were removed The solvent was distilled away under reduced pressure the residue was purified by silica gel column chromatography