Hydrochloric Acid → 5-(4-Chlorophenyl)-5-hydroxypentanoic acid

Participants

Reaction Steps

To a solution of 10.6 g of 4-(4-chlorobenzoyl)butanoic acid and 1.9 g of sodium hydroxide in 50 ml of water was added under ice-cooling 2.7 g of sodium borohydride portionwise over 35 minutes, and the mixture was stirred at room temperature for 24 hours. The mixture was made acidic with diluted hydrochloric acid under ice-cooling, extracted with ether. The ether extract was washed with water and dried. After removal of the solvent, the residue was recrystallized from a mixture of ethyl acetate-n-hexane to give 7.50 g of 5-(4-chlorophenyl)-5-hydroxypentanoic acid as colorless crystals.

Provenance & Evidence