Hydrochloric Acid → 2-[4-(trifluoromethyl)phenoxy]propanoic Acid

Participants

Reaction Steps

To a slurry of 12 g of sodium hydride-oil dispersion (57%) in 100 ml of N,N-dimethylformamide is added 21 g of α,α,α-trifluoro-p-cresol in 10 ml of dimethylformamide and 24 g of 2-bromopropionic acid. After hydrogen evolution, the mixture is heated at 90° C. for 14 hrs. The mixture is cooled, diluted with 100 ml of water, acidified with hydrochloric acid and extracted with ether. The ether extracts are dried (MgSO4) and concentrated to give 23 g of product. A 3.5 g sample is chromatographed over silica gel with solvent hexane-ether-acetic acid (80:20:1) to give 2.3 g of white crystals. Recrystallization from hexane gives crystals, mp 81°-82° C.

Provenance & Evidence