Hexanal → HCID 12960857, compound

Participants

Reaction Conditions

Reaction Steps

30 ml. of dry dimethyl sulfoxide are poured into a 200 ml. of four-necked flask equipped with a stirrer, a dropping funnel, a gas inlet tube, a thermometer and a condenser. 2.5 g. (0.13 moles) of sodium hydroxide (80% oily suspension) are introduced into the flask, and the mixture is stirred at 70° C. under argon temperature until the gas evolution ceases (0.5 hours). The reaction mixture is cooled to room temperature, a solution of 20 g. (0.036 moles) of triphenyl-(11-acetoxy-undecyl)-phosphonium bromide (Formula V, X=Br, Y=COCH3) in 20 ml. of dry dimethyl sulfoxide is added, and the resulting mixture is stirred at room temperature for 0.5 hours. There are added dropwise to the red solution 4 g. (0.04 moles) of hexanel (Formula IV, R=CH3), and the mixture is stirred at room temperature for 15 hours. The reaction mixture is poured onto 60 g. of ice, and extracted with 200 ml. of hexane. The extract is washed successively with water, 10% aqueous sulfuric acid, water, saturated aqueous sodium bicarbonate solution and again with water, dried over magnesium sulfate, filtered, and the solvent is evaporated in vacuo. 2.34 g. (22%) of (Z)-11-heptadecenyl acetate (Formula I, R=CH3) are obtained; b.p.: 122°-125° C./0.05 mmHg.

Provenance & Evidence