Methanol → HCID 20373928, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 22.5 g. of ethyl 2-methyl-3-ethyl-4-ketocyclohexanecarboxylate (all-cis form, m.p. 28°-32°) in 450 ml. of methanol is stirred and maintained at a temperature of 5°-7° C. while a total of 11.0 g. of sodium borohydride is added over a period of 40 minutes. The reaction mixture is stirred at 5° C. for an additional one hour after which a total of 40 ml. of acetic acid is added cautiously to neutralize the base. The methanol solution is evaporated under vacuum to a pasty residue which is shaken with ether and water. The ether phase is washed with aqueous sodium bicarbonate and is dried and evaporated to yield a colorless oil. Upon distillation of the oil, 21.5 g. of ethyl 2-methyl-3-ethyl-4-hydroxycyclohexanecarboxylate is obtained as a mobile oil having a boiling point of 88°-91° at 0.001 mm.

Provenance & Evidence