Hydroxyphenylacetic acid → [4-(4-Nitrophenoxy)phenyl]acetic acid

Participants

Reaction Steps

A mixture of 38 g of p-hydroxyphenylacetic acid, 39.4 g of 4-nitrochlorobenzene and 69 g of anhydrous potassium carbonate in 275 ml of N,N-dimethylacetamide is heated to 155°-160° C. over 2 hours, and maintained at that temperature, under Argon atmosphere for 4 hours with vigorous stirring. On cooling, an orange solid separated. A 1000 g solution of 5% NaHCO3 is added, resulting in a red brown solution. The solution is extracted with 4×100 ml of ether. The aqueous layer is acidified by the dropwise addition of 150 ml of concentrated HCl. A light yellow solid precipitates and is filtered and washed with 1500 ml of H2O to give the product, mp 132°-136° C. A sample is recrystallized from 19:1 methanol-water, to give the product, mp 135°-137° C.

Provenance & Evidence