2-Chlorocyclohexanone → 2-(3-Methoxyphenyl)cyclohexanone

Participants

Reaction Steps

A mixture of 261.8 g of 3-methoxybromobenzene in 500 ml of ether is added dropwise to a 34.0 g sample of magnesium in 600 ml of ether. To the reaction mixture is added a suitable catalyst and the mixture is heated vigorously to initiate the reaction. The prepared Grignard Reagent is cooled in an ice bath while 185.6 g of 2-chlorocyclohexanone in 500 ml of ether is introduced. The ether is removed and xylene added and the xylene solution is refluxed for 1 hour. The solution is poured over ice and dilute hydrochloric acid, the organic layer separated, the aqueous layer extracted with benzene, the organic layer and benzene extracts are combined and washed with dilute sodium hydroxide solution, dried, filtered, and the solvent removed leaving a red oil. The oil is vacuum distilled to give a clear pink liquid of 2-(3-methoxyphenyl)cyclohexanone.

Provenance & Evidence