2-Nitrophenyl benzoate → Benzoxazole, 2-phenyl-

Participants

Reaction Conditions

Reaction Steps

An autoclave is charged with 2.43 g. o-nitrophenyl benzoate, 0.50 g. 5% palladium-on-carbon, 0.25 g. ferric chloride and 20 ml. of acetonitrile, purged with nitrogen, pressurized to 5,000 psig. with carbon monoxide, and heated at 190° C. for 6 hours. Analysis of the reaction mixture by vapor phase chromatography shows that the major component (87%) is 2-phenylbenzoxazole and a minor component is 3-benzoyl-2-benzoxazolinone. The catalyst is removed and the solvent is evaporated. Chromatography of the residual oil on alumina yields 2-phenylbenzoxazole, melting point 100°-102° C., identical with an authentic sample by mixed melting point and infrared spectrum.

Provenance & Evidence