Acetic Acid → 2-n-Hexyl-3-cyanocyclopentanone

Participants

Reaction Conditions

Reaction Steps

In a 3-L three necked flask fitted with a mechanical stirrer, a reflux condenser, a dropping funnel and a thermometer, are placed 83 g of 2-n-hexyl-cyclopentenone, 1.75 L 95% ethyl alcohol and 30 g of glacial acetic acid. The mixture is warmed up with sirring to 35°C and a solution of 65 g of potassium cyanide in 190 ml of water is added over a period of 15 minutes. Stirring is continued for 3 hours, the temperature being maintained at 35°C. The methanol is then distilled off at a reduced pressure the organic layer is separated, and the water phase is extracted with ether. The combined organic layer and other extract are washed with sodium carbonate solution and water and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110°C/0,2 mm, yield 85 g (88%), nD20 1.4658.

Provenance & Evidence