Hydroxyphenylacetic acid → [p-(p-Cyanophenoxy)phenyl]acetic Acid

Participants

Reaction Steps

To a solution of 15.2 g of p-hydroxyphenylacetic acid and 12.1 g of p-fluorobenzonitrile in 125 ml of N,N-dimethylacetamide is added, with vigorous stirring, 27.6 g of anhydrous potassium carbonate. The mixture is heated at 155°-160° C under an Argon atmosphere with rapid stirring for 4 hours. After cooling to room temperature the mixture is poured into 300 ml of saturated NaHCO3. The mixture is extracted with two 100 ml portions of ether. The aqueous layer is acidified with 50 ml of concentrated HCl. The product is filtered washed with water (ca 500 ml) and dried to give a white solid mp 125.5°-127.5° C. A portion is recrystallized from 7:3 methanol-water (10 ml) to give white needles, mp 26.5°-128.5° C.

Provenance & Evidence