Phenylacetone → 3-Phenyl-6-(m-methylphenyl)-5-hexen-2-one

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Reaction Steps

Sodium hydride (6 g., 0.14 mole, oil dispersion) is suspended in glyme (250 ml.) and phenyl acetone (18.6 g., 0.14 mole) in glyme (50 ml.) is added dropwise with stirring. After complete addition the mixture is heated to reflux for one hour. The mixture is cooled in a cold water bath and a solution of m-methylcinnamyl bromide (29.16 g., 0.14 mole) in glyme (50 ml.) is added dropwise. When addition is complete the mixture is refluxed for 20 hours. The cooled mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is dissolved in ether and washed with dilute hydrochloric acid, water and saturated brine. After drying (MgSO4) and evaporation of ether the residue is vacuum distilled and the product is collected at 161°-164°/0.4 mm; 25.24 g.

Provenance & Evidence