Benzene → 3,4-Dimethoxy-2-phenylacetophenone

Participants

Reaction Steps

42.8 Grams (0.32 moles) of aluminum chloride was added in portions to a solution of 45.9 g. (0.2 mole) of homoveratryl chloride and benzene (25 ml.) in methylene chloride (300 ml.). The mixture was then refluxed 1.5 hours, cooled and poured into a mixture comprised of 300 ml. of ice, 100 ml. of water and 225 ml. of concentrated hydrochloric acid. The organic phase was separated and the aqueous layer extracted with chloroform. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and the solvent removed at reduced pressure to give an oil. Chromatography (2×) over alumina (ethyl acetate) followed by treatment with ether gave 3',4'-dimethoxydesoxybenzoin, m.p. 80°-81° C.

Provenance & Evidence