Hydrochloric Acid → 2-Chloro-4-(1-hydroxyoctadecyl)benzoic acid

Participants

Reaction Steps

To 159 mg of product from Example 11 suspended in 10 ml of ethyl alcohol at 0° C. was added 13 mg of sodium borohydride. An additional 10 ml of ethyl alcohol was added and the reaction stirred overnight while allowed to warm to room temperature. An additional 40 mg of sodium borohydride was added followed in about 20 hours by 50 ml of ethanol and 100 mg of sodium borohydride. Stirring was continued for 20 hours whereupon 25 ml of water was added, followed by 20 ml of 10% hydrochloric acid. The organic solvent was removed using a rotary evaporator and the aqueous residue extracted with two 50 ml portions of ethyl ether. The organic extracts were combined, washed with water, dried over sodium sulfate, and filtered. The solvent was removed using a rotary evaporator to give a white solid (150 mg). Recrystallization of the solid from methanol/hexane gave 139 mg of product identical with that disclosed in Example 14 of U.S. Pat. No. 4,469,885.

Provenance & Evidence