Phenylacetaldehyde → 2-Cyclohexen-1-one, 4-phenyl-

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Reaction Steps

A mixture of 19.5 cm3 of phenylacetaldehyde, 16.7 cm3 of methyl vinyl ketone, 0.17 cm3 of 36% sulphuric acid and 85 cm3 of toluene is heated for 1 hour at a temperature in the region of the reflux temperature. After cooling to a temperature in the region of 20° C., 50 cm3 of ethyl acetate are added to the reaction mixture. The resulting mixture is washed with 100 cm3 of saturated aqueous sodium bicarbonate solution and then dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. The residue is purified by flash chromatography on a column of silica [eluent: cyclohexane/ethyl acetate (90/10)] to give 4.7 g of 4-phenylcyclohex-2-enone in the form of a yellow oil, the characteristics of which are as follows:

Provenance & Evidence