Hydrochloric Acid → HCID 178448016, compound

Participants

Reaction Steps

A mixture of 0.303 g of the obtained 1-[trans-4-(trans-4-propenylcyclohexyl)cyclohexyl]-3, 4-difluorobenzene, 5 ml of toluene, 0.31 ml of 3N hydrochloric acid and 45 mg of sodium benzenesulfinate was stirred at 60°-65° C. for 3 hours. Subsequently, the reaction mixture was cooled to room temperature, poured on to 20 ml of 10% sodium hydrogencarbonate solution, and extracted with diethyl ether. The organic phases were washed with water, dried over sodium sulfate, and concentrated. Chromatographic purification of the crude product (0.314 g with an E/Z ratio of 83:16) with hexane/ethyl acetate (vol. 98:2) on silica gel treated with silver nitrate, and subsequent recrystallization from diethyl ether/methanol yielded 0.126 g of 1-[trans-4-(trans-4-(1E-propenyl)cyclohexyl]-cyclohexyl]-3,4-difluorbenzene as colorless crystals with m.p. (C-S ) 49.0° C., S -N 65.6° C., cl.p. (N-I) 159.7° C.; Δε (149° C)=3.22.

Provenance & Evidence