Diethyl Ether → HCID 21258427, compound

Participants

Reaction Steps

A solution of 1-(4-chlorophenyl)cyclobutanecarbonitrile (35 g) in toluene (100 ml) was added dropwise at reflux temperature under nitrogen to a stirred solution of phenethylmagnesium bromide [prepared in the usual manner from phenethyl bromide (45.6 g) and magnesium (6.24 g)] in ether (100 ml). When the addition was completed, ether was distilled from the mixture until the internal temperature rose to 110° C., then stirring at this temperature was continued for 18 hours. The mixture was then cooled to ambient temperature, added to a mixture of ice (200 g) and concentrated hydrochloric acid (100 ml), heated at 95° C. with occasional stirring for 4 hours, and cooled to ambient temperature. The product was extracted into dichloromethane (3×200 ml), and the combined extracts were washed with water (100 ml), saturated aqueous sodium carbonate solution (2×100 ml) and water (100 ml), dried (Na2SO4), and the solvent was removed in vacuo. The residue was distilled to give 1-[1-(4-chlorophenyl)cyclobutyl]-3-phenylpropan-1-one as a yellow oil (38.8 g), b.p. 178-181° C./1.3 mbar.

Provenance & Evidence