Succinic anhydride → 3-(4-Fluorobenzoyl)propionic acid

Participants

Reaction Steps

A suspension of 170 g anhydrous aluminum chloride and 266 g fluorobenzene was stirred under nitrogen at 10° C. while succinic anhydride (54.4 g) was added in small portions. The mixture was stirred 1.5 hours at 10° to 20° C. and then heated on a steam bath for 45 minutes. The mixture was poured onto 1.2 kg crushed ice containing 280 ml 6N HCl. The product was extracted into methylene chloride, which was washed with water, and then back-extracted into 2N NaOH. The basic extract was treated with activated carbon, and acidified with HCl to precipitate title product, 94 g, mp 98.5°-101° C. Recrystallization from methylene chloride/hexane gave 90.6% recovery, mp 99°-101° C.

Provenance & Evidence