Sulfuric Acid → 2-(4-Chlorophenyl)-5-hydroxyoct-1-ene

Participants

Reaction Steps

A solution of 4-(4-chlorophenyl)pent-4-enal (2.0 g) in dry diethyl ether (25 ml) was added to a stirred solution of propylmagnesium iodide [from 1-iodopropane (2.72 g) and magnesium turnings (0.48 g)] in dry diethyl ether (50 ml) under an atmosphere of nitrogen (exotherm). After stirring for 1 hour the reaction mixture was poured into a mixture of ice and dilute sulphuric acid, then extracted with ether. The extracts were washed with water, dried over magnesium sulphate, and concentrated under reduced pressure to give 2-(4-chlorophenyl)-5-hydroxyoct-1-ene (1.9 g, 77%) as a yellow oil.

Provenance & Evidence