Phenylacetyl chloride → 2-Phenylacetophenone

Participants

Reaction Steps

57.0 g (0.30 mole) of n-octylbenzene are dissolved in 500 ml of carbon disulfide, 45.0 g (0.34 mole) of aluminum chloride are added at 0° C., and a solution of 46.4 g (0.30 mole) of phenylacetyl chloride and 50 ml of carbon disulfide are added dropwise at from 0° to 5° C., while stirring. The reaction mixture is stirred for a further 2 hours at from 0° to 5° C. and then for 15 hours without being cooled, after which it is poured carefully onto 1 l of semiconcentrated ice-cold hydrochloric acid. The phases are separated, the organic phase is extracted by shaking with 300 ml of water, the aqueous phase is extracted with three times 300 ml of methylene chloride, and the combined organic phases are dried over sodium sulfate. The solution is filtered and the solvent is distilled off to give 92 g (=100% of theory) of deoxybenzoin as a colorless crystalline mass, which is shown by thin layer chromatography (silica gel/CH2Cl2 : R≈0.95; toluene: R≈0.61) to be sufficiently pure for the subsequent bromination.

Provenance & Evidence