(4-propylphenyl)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:; See reaction.notes.procedure_details.

Procedure: (4-Propylphenyl)methanol (4.93 g) synthesized in Reference Example 36 was dissolved in carbon tetrachloride (65 mL), triphenylphosphine (9.5 g) was added thereto, and the mixture was heated under reflux for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in hexane. The insoluble material was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane) to give the title compound (2.24 g) as a colorless oil. the mixture was heated under reflux for 4 hr The reaction mixture was concentrated under reduced pressure the residue was dissolved in hexane The insoluble material was filtered off the filtrate was evaporated under reduced pressure The residue was purified by silica gel chromatography (elution solvent; hexane)

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

Procedure: Lithium aluminum hydride (1.16 g) was suspended in diethyl ether (100 mL), a solution (50 mL) of 4-propylbenzoic acid (5.0 g) in diethyl ether was added under ice-cooling, and the mixture was heated under reflux for 2.5 hr. The reaction mixture was ice-cooled, and water (3.0 mL) and aqueous sodium hydroxide solution (1 mol/L, 12 mL) were successively added dropwise. After warming to room temperature, the mixture was stirred for 30 min. The reaction mixture was directly filtered through celite, and the filtrate was evaporated under reduced pressure to give the title compound (4.9 g) as a colorless oil. cooling the mixture was heated under reflux for 2.5 hr cooled The reaction mixture was directly filtered through celite the filtrate was evaporated under reduced pressure

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

Procedure: Lithium aluminum hydride (1.16 g) was suspended in diethyl ether (100 mL), a solution (50 mL) of 4-propylbenzoic acid (5.0 g) in diethyl ether was added under ice-cooling, and the mixture was heated under reflux for 2.5 hr. The reaction mixture was ice-cooled, and water (3.0 mL) and aqueous sodium hydroxide solution (1 mol/L, 12 mL) were successively added dropwise. After warming to room temperature, the mixture was stirred for 30 min. The reaction mixture was directly filtered through celite, and the filtrate was evaporated under reduced pressure to give the title compound (4.9 g) as a colorless oil. cooling the mixture was heated under reflux for 2.5 hr cooled The reaction mixture was directly filtered through celite the filtrate was evaporated under reduced pressure

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

Procedure: A solution of sodium borohydride (2.9 g, 76 mmol) and concentrated sulfuric acid in ether (prepared by adding 2.0 ml of concentrated sulfuric acid to 4.0 ml of ether) was added dropwise to a solution of p-n-propylbenzoic acid (5.0 g, 32 mmol) in tetrahydrofuran (20 ml) cooled to 0° C. keeping the temperature of the reaction system below 20° C., and then this mixture was stirred at room temperature for 3 hours. After the mixture was cooled on ice, methanol and 1 N sodium hydroxide were added, and this mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give the title compound (4.33 g). This compound was used in the following reaction without purification. the temperature of the reaction system below 20° C. were added this mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure

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

Procedure: A solution of sodium borohydride (2.9 g, 76 mmol) and concentrated sulfuric acid in ether (prepared by adding 2.0 ml of concentrated sulfuric acid to 4.0 ml of ether) was added dropwise to a solution of p-n-propylbenzoic acid (5.0 g, 32 mmol) in tetrahydrofuran (20 ml) cooled to 0° C. keeping the temperature of the reaction system below 20° C., and then this mixture was stirred at room temperature for 3 hours. After the mixture was cooled on ice, methanol and 1 N sodium hydroxide were added, and this mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give the title compound (4.33 g). This compound was used in the following reaction without purification. the temperature of the reaction system below 20° C. were added this mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure

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

Procedure: A solution of sodium borohydride (2.9 g, 76 mmol) and concentrated sulfuric acid in ether (prepared by adding 2.0 ml of concentrated sulfuric acid to 4.0 ml of ether) was added dropwise to a solution of p-n-propylbenzoic acid (5.0 g, 32 mmol) in tetrahydrofuran (20 ml) cooled to 0° C. keeping the temperature of the reaction system below 20° C., and then this mixture was stirred at room temperature for 3 hours. After the mixture was cooled on ice, methanol and 1 N sodium hydroxide were added, and this mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give the title compound (4.33 g). This compound was used in the following reaction without purification. the temperature of the reaction system below 20° C. were added this mixture was extracted with ethyl acetate The ethyl acetate layer was washed with saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure

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

Procedure: In 50 ml of chloroform was dissolved 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol synthesized in the step (ii), and 8.10 g (68.1 mmol) of thionyl chloride was added to the mixture. The mixture was subjected to reaction at a room temperature for 24 hours. After the completion of the reaction, the chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water. Chloroform was removed from the chloroform phase to give 9.40 g (55.8 mmol) of 4-n-propylbenzylchloride. was added to the mixture The mixture was subjected to reaction at a room temperature for 24 hours After the completion of the reaction the chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water Chloroform was removed from the chloroform phase

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

Procedure: Dried tetrahydrofuran (50 ml) in which 10.4 g (58.4 mmol) of 4-n-propylbenzoic acid methyl ester synthesized in step (i) was dissolved was dropwise added to 50 ml of dried tetrahydrofuran containing suspension of lithium aluminium hydride (1.54 g: 40.5 mmol) at a temperature of not more than 10° C. with cooling with ice, and reaction was carried out at a room temperature overnight. After the completion of the reaction, an excess amount of lithium aluminium hydride was reacted with methanol with cooling with ice. Next water and an aqueous solution of hydrochloric acid were successively added to the reaction mixture, and the resultant was extracted with hexane. After the hexane phase was washed with water, hexane was removed from the hexane phase to give 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol. with cooling with ice, and reaction After the completion of the reaction with cooling with ice the resultant was extracted with hexane After the hexane phase was washed with water, hexane was removed from the hexane phase

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

Procedure: Dried tetrahydrofuran (50 ml) in which 10.4 g (58.4 mmol) of 4-n-propylbenzoic acid methyl ester synthesized in step (i) was dissolved was dropwise added to 50 ml of dried tetrahydrofuran containing suspension of lithium aluminium hydride (1.54 g: 40.5 mmol) at a temperature of not more than 10° C. with cooling with ice, and reaction was carried out at a room temperature overnight. After the completion of the reaction, an excess amount of lithium aluminium hydride was reacted with methanol with cooling with ice. Next water and an aqueous solution of hydrochloric acid were successively added to the reaction mixture, and the resultant was extracted with hexane. After the hexane phase was washed with water, hexane was removed from the hexane phase to give 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol. with cooling with ice, and reaction After the completion of the reaction with cooling with ice the resultant was extracted with hexane After the hexane phase was washed with water, hexane was removed from the hexane phase

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