4-Methylbenzoyl Chloride → 4-Methoxy-3,4'-dimethylbenzophenone

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Reaction Steps

p-Toluoyl chloride (15.5g, 0.10 mole) is added dropwise at room temperature over a 1 hour period to a mixture of o-methylanisole (15.3 g, 0.125 mole) and aluminum chloride (AlCl3, 37.3g, 0.28 mole) in carbon disulfide (CS2, 50 ml) in a flask fitted with a stirrer, addition funnel, drying tube and reflux condenser. The reaction mixture is then refluxed for 1 hour, cooled and the carbon disulfide removed in vacuo. The residue is then slurried in methylene chloride and poured into 400 g of cracked ice containing 20 ml of concentrated hydrochloric acid. This mixture is then transferred to a separatory funnel and extracted with additional methylene chloride (3 × 15 ml) and the methylene chloride extract dried (anhydrous MgSO4) prior to concentrating in vacuo. The residue was then triturated with benzene. The benzene extract is then diluted with hexane which results in precipitation of 2.5 g. of product (10%), m.p. 73°-5°C.

Provenance & Evidence