Hydrochloric Acid → Methyl 3-hydroxydecanoate

Temperature

60 °C

At room temperature, a three-neck flask equipped with a reflux condenser, internal thermometer, dropping funnel and stirrer under nitrogen protective gas was initially charged with 7.1 g of zinc powder (108 mmol) in 42 ml of ethyl acetate. After 1.7 ml of trimethylchlorosilane (13.4 mmol) had been added, the mixture was heated to 60° C. for 15 min, then allowed to cool to 55° C. and 15.3 g of undiluted methyl bromoacetate (100 mmol) were subsequently added dropwise within 7 min, and the temperature was maintained at 65° C. by external cooling. The mixture was then stirred at 50° C. for 15 min. After cooling to 0° C., 10.7 g of undiluted octanal (83 mmol) were added, and the temperature was maintained at 5° C. by external cooling. After stirring had been continued at 50C for 30 min, 25° C. for 2 h and 40° C. for 20 min, the mixture was cooled to 0° C., acidified with 30 ml of 10% hydrochloric acid to a pH of 1 and the mixture was stirred for 10 min. Excess zinc was then filtered off and the organic phase removed. The organic phase was then stirred with 10 ml of concentrated ammonia solution at 0° C. for 10 min. After the phase separation, drying was effected over sodium sulfate and the solvent was distilled off under reduced pressure. Methyl 3-hydroxydecanoate was obtained in a yield of 14.2 g (84% of theory) and had a boiling point of 59° C. (0.04 mbar).

1. customAt room temperature, a three-neck flask equipped with a reflux condenser
2. temperatureto cool to 55° C.
3. temperaturethe temperature was maintained at 65° C. by external cooling
4. temperatureAfter cooling to 0° C.
5. temperaturethe temperature was maintained at 5° C. by external cooling
6. stirringAfter stirring
7. temperaturethe mixture was cooled to 0° C.
8. stirringthe mixture was stirred for 10 min
9. filtrationExcess zinc was then filtered off
10. customthe organic phase removed
11. stirringThe organic phase was then stirred with 10 ml of concentrated ammonia solution at 0° C. for 10 min
12. customAfter the phase separation
13. customdrying
14. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-41f04e99003f4c579a48c9a72bc177de

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06603034B2