Hydrochloric Acid → 1-Benzoylnaphthalene

Participants

Reaction Steps

To 10.3 g (65 mMol) of bromobenzene in 50 mL of diethyl ether, magnesium turnings were added. The reaction was initiated by adding a few crystals of iodine to about 5 mL of the bromobenzene solution, and warming gently. The remainder of the bromobenzene was then added at such a rate as to maintain a mild reflux. When the reaction had abated, 1-naphthonitrile was added slowly in 50 mL of diethyl ether. The mixture was allowed to stir at room temperature overnight. Water was added, and the mixture acidified to pH 1 with concentrated hydrochloric acid. Methylene chloride was added and the mixture was heated under reflux overnight. The layers were separated, and the organic layer was washed with brine and dried over magnesium sulfate. The subtitled product was crystallized from methylene chloride/hexane, then further purified by medium pressure column chromatography on silica gel, eluting with ethyl acetate:hexane/5:95. The desired product was obtained as a white crystalline solid (4.38 g; 29% yield).

Provenance & Evidence