Diethyl Ether → 3-Allyl-4-hydroxybenzonitrile

Participants

Reaction Steps

A solution of allyl 4-cyanophenyl ether (12 g) in diphenylether (20 ml) was heated at 260° C. for 30 minutes. The reaction mixture was cooled to ambient temperature, diethyl ether was added and the mixture was extracted with 1M aqueous sodium hydroxide solution. The aqueous phase was separated, acidified with 2M aqueous hydrochloric acid solution and extracted with diethyl ether. The organic phase was separated, dried (MgSO4) and evaporated to give 2-allyl-4-cyanophenol as a solid (11.4 g), m.p. 70° C.; microanalysis, found: C, 73.7; H, 5.6; N, 9.2%; C10H9NO. 0.25H2O requires: C, 73.4; H, 5.8; N, 8.6%; NMR: 3.2-3.5(2H,d), 5.0-5.1(2H,m), 5.85-6.05(1H,m), 6.9-7.0(1H,d), 7.4-7.5(2H,m) and 10.6(1H,s).

Provenance & Evidence