Benzenepropanol, 4-hydroxy-3-methoxy- (9CI) → HCID 68988319, compound

Temperature

50 °C

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.

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

ORD record

ord-9d84d1feb4044f09a9f12c2bf71a3ade

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08212068B2