Diethyl Malonate → Diethyl p-isopropylbenzylmalonate

Participants

Reaction Steps

Diethyl malonate was added dropwise at 20°-25° C. to a stirred suspension of sodium hydride (1 equi) in dry DMSO. The mixture was stirred until the evolution of hydrogen had ceased (ca. 1 hour), then a solution of p-isopropylbenzyl bromide (1 equiv.) (prepared from p-isopropylbenzyl alcohol and PBr3) in dry DMSO added dropwise with stirring. After stirring at room temperature for 1.5 hours the mixture was heated on the steam bath for 0.5 hour until a clear solution was obtained. The mixture was poured onto ice, extracted several times with ether and the extracts combined and washed with water and brine, dried (MgSO4) and evaporated in vacuo. The residual oil was distilled, collecting the fraction b.p. 160°-170° (2-3 mm).

Provenance & Evidence