Water → Homovanillyl 8-methylnonanoate

Temperature

50 °C

Homovanillyl alcohol (769 mg, 4.57 mmol), 8-methylnonanoic acid (751 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 without plugging the flask. After stirring with heating for 2 to 3 hr, attachment of water onto the upper wall of the flask was observed. The reaction mixture was allowed to cool to room temperature, ethyl acetate (25 ml) was added, and Novozyme 435 and the precipitated insoluble material were removed by filtration. Ethyl acetate (50 ml) was added to the filtrate, 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 (preparative thin layer chromatography) (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 homovanillyl 8-methylnonanoate (1.31 g, yield 93.2%) as a colorless oil.

1. customplaced in a flask
2. stirringAfter stirring
3. temperaturewith heating for 2 to 3 hr
4. temperatureto cool to room temperature
5. customNovozyme 435 and the precipitated insoluble material were removed by filtration
6. additionEthyl acetate (50 ml) was added to the filtrate
7. washthe 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)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationMagnesium sulfate was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure
11. stirringwas stirred with ethyl acetate (100 ml) for 30 min for extraction
12. filtrationThe silica gel was filtered off
13. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-8a00a73361ba47f08999472e907f73e1

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765809B2