Hydrochloric Acid → 4-(4-Fluorophenyl)-4-hydroxybutanoic acid

Participants

Reaction Conditions

Reaction Steps

Commercial γ-(p-fluorophenyl)-γ-butyrolactone, 18.0 g. (0.10mole) was added to a solution of 14.0 g. (0.35 mole) of sodium hydroxide in100 ml. of water and the mixture heated at reflux for 40 minutes. After cooling to 0° C., 70 ml. of 6 N hydrochloric acid was added at 0°-15° C. for one hour. The white solid which formed was filtered, washed with pentane and air dried to afford racemic-4-hydroxy-4-(p-fluorophenyl)butyric acid, 18.43 g., (93% yield). When heated to temperatures of about 100° C., the hydroxy acid was converted back to the starting lactone.

Provenance & Evidence