2,6-Dichlorobenzoyl chloride → 2,6-Dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone

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Reaction Conditions

Reaction Steps

Aluminum chloride (14.67 g, 0.1 mol), 2,6-dichlorobenzoyl chloride (20.95 g, 0.1 mol) and a solution of 3,4,5-trimethoxytoluene (18.22 g, 0.1 mol) in dichloromethane (50 ml), are slowly and consecutively added to dichloromethane stirred at 0° C., stirred for 1 h at ice bath temperatures and for 16 h at room temperature, and poured into ice. The organic layer is separated, washed with dilute hydrochloric acid and water, dried, and, after addition of silica gel (100 g), concentrated in vacuo. A flash chromatography column is packed with silica gel (400 g) and the charged silica gel is layered on top of that. Elution with petrol ether/ethyl acetate (90/10, 1 l; 80/20, 1 l; 50/50, 1l) yields 2,6-dichloro-3'4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone, 10.35 g, (30% y).

Provenance & Evidence