2,3-di(butanoyloxy)propyl butanoate

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

Procedure: 1-(3-Pyridyl)ethanol (8.9 g), tributyrin (24.0 g) and an enzyme (Lipase CES made by Amano Seiyaku K. K.) (3.6 g) were agitated at 37° C. for 190 hours, followed by filtering off the enzyme and subjecting the filtrate to silica gel column chromatography using toluene as solvent to obtain (S)-1-(3-pyridyl)ethanol (3.0 g). According to a high-speed liquid chromatography using an optical resolution column (CHIRAL CEL OB, trademark of product made by Daicel Co., Ltd.), its optical purity was 80% ee or higher. by filtering off the enzyme

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

Procedure: Racemic(±)-4-octyloxy-4'-(1-hydroxyethyl)biphenyl (m.p. 110.9°-111.9° C.) and tributyrin were biochemically transesterified. The obtained 7.0 g (21 mmol) of optically active (-)-4-octyloxy-4'-(1-hydroxyethyl)biphenyl (m.p. 123.6° C., [α]D 24.5 -27.0° (c 1.0, CHCl3)), 7.5 g(36 mmol) of N,N'-dicyclohexylcarbodiimide (abbreviated as DCC) and 1.0 g of 4-dimethylaminopyridine (abbreviated as DMAP) were dissolved in 200 ml of dichloromethane. To the solution, 3.4 g (29 mmol) of caproic acid was added, and the mixture was stirred for six hours at room temperature. The deposited crystals were filtered, 200 ml of water was added to the filtrate, and the organic layer was separated. 6N hydrochloric acid was added to the organic solution, and then the solution was neutralized with the aqueous solution of 2N sodium hydroxide. The neutralized solution was washed with water until the washed water became neutral. The solvent and low-boiling fractions were distilled away from the obtained solution. The residue was recrystallized from ethanol and the desired (-)-4-octyloxy-4'-(1-hexanoyloxyethyl)biphenyl 6.8 g was obtained. The melting point of the obtained biphenyl was 60.8° C. and its specific optical rotation was -78.4° at 25.3° C. for D line (c 0.88, C2H5OH). The deposited crystals were filtered 200 ml of water was added to the filtrate the organic layer was separated 6N hydrochloric acid was added to the organic solution The neutralized solution was washed with water until the washed water The solvent and low-boiling fractions were distilled away from the obtained solution The residue was recrystallized from ethanol

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An enzyme (Amano CES, tradename of a lipase made by Amano Seiyaku Company) (10 g), ±-1-(2-bromophenyl)ethanol (7.0 g, 35 mmol) and tributyrin (15.9 g, 52.5 mmol) were placed in a three-necked flask, followed by agitating these materials at 35° C. for 15 days, stopping the reaction, thereafter filtering off the enzyme, concentrating the filtrate and subjecting the concentrate to silica gel chromatography to isolate the respective objective products. As a result, (S)-1-(2-bromophenyl)ethanol ([α]D23.5° C. : -26.3° (C 3.72, CHCl3)) (2.6g) and R-1-(2-bromophenyl)-1'-butanoyloxyethane (25 g) were obtained, followed by hydrolyzing the latter compound to obtain R-1-(2-bromophenyl)ethanol ([α]D23.5° : 30 33.5° (C 3.52, CHCl3)) (1.7 g). were placed in a three-necked flask the reaction filtering off the enzyme concentrating the filtrate concentrate to silica gel chromatography to isolate the respective objective products

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

Procedure: 1-(3-Pyridyl)ethanol (8.9 g), tributyrin (24.0 g) and an enzyme (Lipase CES made by Amano Seiyaku K. K.) (3.6 g) were agitated at 37° C. for 190 hours, followed by filtering off the enzyme and subjecting the filtrate to silica gel column chromatography using toluene as solvent to obtain (S)-1-(3-pyridyl)ethanol (3.0 g). According to a high-speed liquid chromatography using an optical resolution column (CHIRAL CEL OB, trademark of product made by Daicel Co., Ltd.), its optical purity was 80% ee or higher. by filtering off the enzyme