2-Tetralone → 2-Phenylnaphthalene

Participants

Reaction Conditions

Reaction Steps

A mixture of 14.6 g. of 2-tetralone, 20 g. of phenylmagnesium bromide, and 200 ml. of diethyl ester is stirred for four hours and then refluxed for one hour. The mixture is acidified with the addition of 200 ml. of 1 N hydrochloric acid, filtered, and extracted with diethyl ether. The extracts are combined, washed with water to neutrality, filtered, dried and evaporated; unchanged 2-tetralone is removed by distillation. The residue, containing 2-phenyl-3,4-dihydronaphthalene is mixed with 25 g. of 5 percent palladium-on-charcoal catalyst; the resulting mixture is heated to 200° C for six hours, cooled, diluted with 250 ml. of chloroform, filtered, and evaporated to give 2-phenylnaphthalene.

Provenance & Evidence