Mandelic Acid → 2-[4-(4-Chlorophenyl)benzyloxy]-2-phenylacetic acid

Participants

Reaction Steps

(+)-Mandelic acid (3.04 g.) was added to a stirred suspension of sodium hydride (1.92 g., 50% w/w dispersion in mineral oil) in dimethyl sulphoxide (50 ml.) at 15°-20° C., and the mixture was then stirred at the same temperature for 4 hours. 4-(4-Chlorophenyl)benzyl chloride (4.74 g.) was then added to the mixture and stirring was continued at room temperature for 1 hour. The resultant mixture was adjusted to pH 1-3 by careful addition of N-hydrochloric acid, and then extracted thoroughly with ether. The combined extracts were washed with water, dried (MgSO4) and evaporated. The solid residue obtained was recrystallised from a mixture of ethyl acetate and hexane to give (+)-2-[4-(4-chlorophenyl)benzyloxy]-2-phenylacetic acid (3.45 g.), m.p. 119°-121° C., [α]D25 +104° (C=1,CHCl3).

Provenance & Evidence