Formic Acid → HCID 178497880, compound

Participants

Reaction Steps

A mixture of 123 g of 4-[4-(methoxymethylidene)cyclohexyl]benzoic acid methyl ester 1000 ml of toluene and 500 ml of formic acid was stirred vigorously at room temperature overnight. The formic acid phase was separated. The toluene phase was washed neutral with water, dried over sodium sulfate, filtered and concentrated. The crude trans/cis-mixture obtained was dissolved in 600 ml of methanol. The solution was added dropwise at 3° C. within 10 minutes to 1.2 1 of 0.1N methanolic potassium hydroxide solution while gassing with nitrogen. The reaction mixture was stirred at 3° C. for a further 1 hour, then poured on to ice/water and extracted with diethyl ether. The organic phases were washed neutral with water, dried over sodium sulfate, filtered and concentrated. Recrystallization of the residue from tert. butyl methyl ether yielded 88.5 g of 4-(trans-4-formylcyclohexyl)benzoic acid methyl ester with m.p. 84°-85° C.

Provenance & Evidence