Methanol → Methyl 11-bromoundecanoate

With cooling and stirring, 4.0 ml (0.099 mole) of methanol was added to 25.6 grams (0.090 mole) of 11-bromoundecanoic acid chloride. Triethylamine, 13.8 ml (0.099 mole) was then added dropwise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred for 16 hours. The reaction mixture was diluted with diethyl ether and was washed in turn with water, an aqueous solution saturated with sodium bicarbonate, water, and an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 23.9 grams of methyl 11-bromoundecanoate. The nmr spectrum was consistent with the proposed structure.

1. temperatureWith cooling
2. additionUpon completion of addition the reaction mixture
3. stirringstirred for 16 hours
4. washwas washed in turn with water
5. dry with materialThe organic layer was dried with sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-c3a18c28de1042118fc5850051cfbb0e

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04950666