Hydrochloric Acid → 3-(p-Cyclohexyloxybenzoyl)propionic acid

Participants

Reaction Steps

A solution of succinic anhydride (20 g.) and phenoxycyclohexane (35.1 g.) in 1,2-dichloroethane (250 ml.) was stirred at 0°C and treated with powdered anhydrous aluminium chloride (58.2 g.) and stirring was continued for 5 hours at 0°-5°C. It was then poured carefully with stirring into ice-water (1 liter) containing concentrated hydrochloric acid (100 ml.). The organic layer was separated, washed with water and extracted with a solution of sodium hydroxide (8 g.) in water (250 ml.). The alkaline extract was adjusted to pH 4-6 by the addition of dilute hydrochloric acid to yield the product (6.8 g.), m.p. 190°-192°C after crystallisation from aqueous methanol.

Provenance & Evidence