Ethanol → 4,8,12-Trimethyltrideca-3,7,11-trienoic acid

Participants

Reaction Steps

A mixture of 469 g (2.02 moles) farnesyl cyanide, 287 g potassium hydroxide, 2,500 ml ethanol and 340 ml water were heated under reflux. After 5 hours, the ethanol was evaporated and the residue poured into 10 liters of water. The aqueous solution so obtained was twice extracted with 1 liter diethyl ether, the extracts being discarded, and thereafter acidified with 20% sulfuric acid. Then, the free acid was extracted with diethyl ether. The etheric solution was again washed with water and dried with sodium sulfate. After evaporation of the ether, 419 g (83% of the theoretical) of homofarnesic acid were obtained as a yellow oil.

Provenance & Evidence