Dimethyl Sulfide → HCID 11172431, compound

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Reaction Steps

A mixture of 27.8 g (207.9 mmol) N-chlorosuccinimide and 450 ml of toluene is cooled to -20° to -25° and 20.4 ml of dimethylsulfide (277.3 mmol) is added all at once. The mixture is stirred at -20° for 30 min. A solution of 33 g (138.6 mmol) of (9Z, 11E)-9,11-hexadecadien-1-ol in 10 ml of toluene is added over a period of 20 min. at -15°, with occasional warming to -5°. After addition is complete, the mixture is stirred at -15° for 20 min., then warmed to -5°, and then cooled to -50° as 38.7 ml (277.3 mmol) of triethylamine is added in one portion. The suspension is allowed to warm to 0° and is then quenched with water. The phases are separated and the aqueous layer is extracted with ether (2X). The combined organic phases are washed with 2 N sulfuric acid, water, saturated sodium bicarbonate and brine and dried over sodium sulfate. Purification by chromatography on a column of silica gel, eluting with hexane, then 10% ether/hexane, followed by recrystallization from hexane at -78° yields pure (9Z,11E)-9,11-hexadecadienal.

Provenance & Evidence