2,6-Dichlorobenzoyl chloride → (2,6-Dichlorophenyl)(4-methylphenyl)methanone

Participants

Reaction Steps

An 80° C., stirred solution of 2,6-dichlorobenzoyl chloride (17.3 g, 82.6 mmol) in toluene (30 ml) was treated in portions with aluminum chloride (11.0 g, 82.3 mmol). After 12 hours at 80° C., the mixture was cooled, quenched with ice water and concentrated hydrochloric acid (10 ml), and separated. The aqueous phase was extracted with diethyl ether (2×150 ml) and the combined organic phases were washed twice with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under vacuum. The residue was crystallized from hexane to provide 12.6 g (58%) 4-(2,6-dichlorobenzoyl)toluene, m.p. 109°-111.5° C.

Provenance & Evidence