Mesitylene → Methanone, (4-chlorophenyl)(2,4,6-trimethylphenyl)-

Participants

Reaction Conditions

Reaction Steps

A stirred 0° C. solution of mesitylene (7.21 g, 60.0 mmol) and 4-chlorobenzoyl chloride (10.55 g, 60.0 mmol) in carbon disulfide (130 ml) was treated with aluminum chloride (8.83 g, 66.1 mmol) in portions over 10 minutes. The mixture was stirred 75 minutes at 0° C., warmed to ambient temperature over 30 minutes, refluxed 10 hours, kept at ambient temperature 6 hours, cooled to 0° C., and quenched by addition of ice (250 g) and concentrated hydrochloric acid (50 ml). The mixture was extracted twice with diethyl ether and the combined extracts were washed with water (3X), saturated aqueous sodium carbonate, and brine, dried over anhydrous magnesium sulfate, and evaporated to dryness at 30° C. under vacuum. The residue was crystallized from methanol and dried to provide 9.61 g (62%) 4-chlorobenzoylmesitylene, m.p. 65.5°-66.5° C.

Provenance & Evidence