Water → HCID 178445662, compound

Participants

Reaction Conditions

Reaction Steps

Sodium (7.5 g, 0.33 mol) was dissolved in anhydrous ethanol (200 ml) and ethyl cis-4-n-butylcyclohexanecarboxylate (13) was added. The reaction mixture was heated at reflux for 16 hr and was then cooled to 20° C. Water (38 ml) was added and the mixture was re-heated to reflux for a further 24 hr. The resulting mixture was evaporated to a small volume and the residue was dissolved in water (115 ml). The solution was acidified using concentrated hydrochloric acid and the product was then extracted into dichloromethane (4×50 ml). The combined dichloromethane extracts were evaporated to give predominantly trans-4-n-butylcyclohexanecarboxylic acid (11, 45.6 g).

Provenance & Evidence