Dimethyl Sulfide → (Z,Z)-11,13-Hexadecadienal

Participants

Reaction Steps

To a mixture of N-chlorosuccinimide (16.8 g, 0.126 mol) and 260 ml of toluene, cooled to 31 20° to -25°, under nitrogen, was added 12.3 ml of dimethylsulfide (10.4 g, 0.167 mol) with stirring. The mixture was stirred for 30 min, then the dienol VI (20 g, 0.0839 mol) in 50 ml of toluene was added gradually over a period of 20 min at -20° to -25°. The mixture was held at -20° for about 20 min, warmed briefly to -5°, then cooled rapidly to -50° and 23.5 ml of triethylamine was added with vigorous stirring. The mixture was warmed to -15° and then to 0°, and after about 10 min 75 ml of water was added. The organic phase was separated, washed with 1 N sulfuric acid, water, dilute sodium bicarbonate and brine, dried over sodium sulfate, and solvent evaporated. The product was chromatographed on 40 g Woelm silica using 10% ether in hexane. The crude aldehyde was crystallized twice from hexane at -50° to yield (11Z,13Z)-11,13-hexadecadien-1-al, m.p. 7°-8°.

Provenance & Evidence