DIHYDROCONIFERYL ALCOHOL

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-(3-Methoxy-4-hydroxyphenyl)propyl alcohol (833 mg, 4.57 mmol), 8-methylnonanoic acid (753 mg, 4.35 mmol) and Novozyme 435 (51 mg) were measured and placed in a flask (25 ml). The mixture was stirred with heating in an oil bath at 50° C. for 16 hr while reducing the pressure by an aspirator. The reaction mixture was allowed to cool to room temperature, n-hexane (25 ml) was added, and Novozyme 435 and the precipitated insoluble material were removed by filtration. N-hexane (50 ml) was added, and the mixture was washed with 5% aqueous citric acid solution (25 ml×2), saturated brine (25 ml), 5% aqueous sodium hydrogen carbonate solution (25 ml×2) and saturated brine (25 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was developed by PTLC (n-hexane:ethyl acetate=3:1), and silica gel containing the object product was stirred with ethyl acetate (100 ml) for 30 min for extraction. The silica gel was filtered off, and the filtrate was concentrated under reduced pressure to give 3-(3-methoxy-4-hydroxyphenyl)propyl 8-methylnonanoate (1.40 g, yield 95.4%) as a colorless oil. placed in a flask to cool to room temperature Novozyme 435 and the precipitated insoluble material were removed by filtration N-hexane (50 ml) was added the mixture was washed with 5% aqueous citric acid solution (25 ml×2), saturated brine (25 ml), 5% aqueous sodium hydrogen carbonate solution (25 ml×2) and saturated brine (25 ml) dried over anhydrous magnesium sulfate Magnesium sulfate was filtered off the filtrate was concentrated under reduced pressure was stirred with ethyl acetate (100 ml) for 30 min for extraction The silica gel was filtered off the filtrate was concentrated under reduced pressure

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-(3-Methoxy-4-hydroxyphenyl)propyl alcohol (833 mg, 4.57 mmol), 8-methylnonanoic acid (753 mg, 4.35 mmol) and Novozyme 435 (51 mg) were measured and placed in a flask (25 ml). The mixture was stirred with heating in an oil bath at 50° C. for 16 hr while reducing the pressure by an aspirator. The reaction mixture was allowed to cool to room temperature, n-hexane (25 ml) was added, and Novozyme 435 and the precipitated insoluble material were removed by filtration. N-hexane (50 ml) was added, and the mixture was washed with 5% aqueous citric acid solution (25 ml×2), saturated brine (25 ml), 5% aqueous sodium hydrogen carbonate solution (25 ml×2) and saturated brine (25 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was developed by PTLC (n-hexane:ethyl acetate=3:1), and silica gel containing the object product was stirred with ethyl acetate (100 ml) for 30 min for extraction. The silica gel was filtered off, and the filtrate was concentrated under reduced pressure to give 3-(3-methoxy-4-hydroxyphenyl)propyl 8-methylnonanoate (1.40 g, yield 95.4%) as a colorless oil. placed in a flask to cool to room temperature Novozyme 435 and the precipitated insoluble material were removed by filtration N-hexane (50 ml) was added the mixture was washed with 5% aqueous citric acid solution (25 ml×2), saturated brine (25 ml), 5% aqueous sodium hydrogen carbonate solution (25 ml×2) and saturated brine (25 ml) dried over anhydrous magnesium sulfate Magnesium sulfate was filtered off the filtrate was concentrated under reduced pressure was stirred with ethyl acetate (100 ml) for 30 min for extraction The silica gel was filtered off the filtrate was concentrated under reduced pressure