Water → 1-(2-Oxo-2-phenyl-ethyl)-3,4-dihydro-1H-naphthalen-2-one

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Reaction Steps

A solution of 20 g. (0.1 mole) of phenacyl bromide and 65 ml. of toluene was added during 30 minutes to a boiling, stirred solution of 20 g. (0.1 mole) of 1-(3,4-dihydro-2-naphthyl)pyrrolidine and 50 ml. of toluene. The mixture was heated under reflux for 3 hours, diluted with 50 ml. of water, refluxed for 4 hours and cooled. The layers were separated, the aqueous phase was extracted with benzene, and the organic solution was dried and concentrated to an oil. Crystallization from 30°-60°-petroleum ether-ether gave 16.7 g. (63%) of tan crystals, m.p. 48°-52°.

Provenance & Evidence