Hydrochloric Acid → 1-(4-(methylthio)phenyl)-2-phenylethanone

Participants

Reaction Steps

To a solution of 46.8 g (0.030 mole) of phenylacetyl chloride in dry methylene chloride (330 ml) was added 37.6 g (0.030 mole) of thioanisole. The solution was cooled to 5° in an ice-acetone bath, and anhydrous aluminum chloride (40.9 g, 0.031 mole) was added portionwise over 30 minutes at a rate to maintain the temperature constant at 5°. The reaction mixture was stirred at 5° for 3.5 hours, after which time the mixture was carefully poured into 1300 ml of aqueous 1N HCl and was stirred overnight. The layers were separated and the aqueous layer was extracted with methylene chloride (2×1l). The organic fractions were combined and washed with 1N hydrochloric acid (2×500 ml), 5% aqueous sodium hydroxide (2×500 ml) and brine (2×500 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The crystalline product was collected by filtration and washed with cold ethanol to afford 65.3 g (89%) of 2-phenyl-1-(4-methylthiophenyl)ethanone as a white solid, m.p. 98°-100°.

Provenance & Evidence