Formic Acid → HCID 178497880, compound

Participants

Reaction Steps

A mixture of 123 g of methyl 4-[4-(methoxymethyl idene)-cyclohexyl]benzoate, 1 l 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 cis/trans mixture obtained was dissolved in 600 ml of methanol. The solution was added dropwise while gassing with nitrogen at 3° C. within 10 minutes to 1.2 l of a 0.1N methanolic potassium hydroxide solution. 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 gave 88.5 g of methyl 4-(trans-4-formylcyclohexyl)-benzoate with m.p. 84°-85° C.

Provenance & Evidence