Lithium Hydroxide → m-Phenylenediacetic acid

Participants

Reaction Steps

Dimethyl-3-carboxyphenyl acetic acid (870 mg) in 10 ml tetrahydrofuran was treated with lithium hydroxide (8.5 ml, 0.5M solution) at 0° C. After stirring at room temperature for 4 h, all solvent was evaporated, and the residue partitioned between saturated sodium hydrogen carbonate and ethyl acetate. The aqueous layer was separated, acidified (1N HCl) and extracted with dichloromethane (2×25 ml). The combined organic layers were dried (MgSO4) and solvent removed to leave 3-(carboxymethyl)phenyl acetic acid, mp 96°-98° C.

Provenance & Evidence