Hydrochloric Acid → HCID 178444556, compound

Participants

Reaction Steps

A mixture of 1.29 g of 4-(1E-pentenyl)cyclohexanecarboxylic acid and 20 ml of a 11 percent (wt./vol.) solution of potassium hydroxide in diethylene glycol was boiled at reflux for 20 hours while gassing with argon. The reaction mixture was subsequently made slightly acid with 25 percent hydrochloric acid and partitioned three times in water/ethylene chloride. The organic extracts were washed twice with water and the wash-water was back-extracted with methylene chloride. The organic phases were dried over magnesium sulphate and freed from solvent on a rotary evaporator. Recrystallization of the dark brown, crystallizing oil obtained (1.17 g) from 50 ml of petroleum ether at -78° C. gave 0.44 g of trans-4-(1E-pentenyl)cyclohexanecarboxylic acid as pale brown crystals. The mother liquor containing 0.695 g of crude cis/trans-4-(1-E-pentenyl)-cyclohexanecarboxylic acid was not worked-up.

Provenance & Evidence