Hydrochloric Acid → HCID 178444556, compound

Participants

Reaction Steps

A mixture of 1.29 g of 4-(trans-1-pentenyl)cyclohexanecarboxylic acid and 20 ml of a 11% (wt./vol.) solution of potassium hydroxide in diethylene glycol was boiled at reflux for 20 hours while gassing with argon. The mixture was subsequently made slightly acid with 25% hydrochloric acid and partitioned three times in water/methylene 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 resulting, dark brown, crystallizing oil (1.17 g) from 50 ml of petroleum ether at -78° C. gave 0.44 g of trans-4-(trans-1-pentenyl)cyclohexanecarboxylic acid as pale brown crystals. The mother liquor containing 0.695 g of crude cis/trans-4-(trans-1-pentenyl)cyclohexanecarboxylic acid was not worked-up.

Provenance & Evidence