Potassium Cyanide → 1,3-Dioxolane-2-propiononitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-bromoethyl)-1,3-dioxolane (8.14 g, 45 mmol), potassium cyanide (5.85 g, 90 mmol), and 18-crown-6 (30 mg) in 30 mL of dimethylformamide was stirred for 72 hours at 23° C. The reaction mixture was filtered, diluted with 70 mL of dichloromethane and washed twice with 10 mL of water. The organic phase was dried over magnesium sulfate and distilled under vacuum to yield 3.2 g of 2-(2-cyanoethyl)-1,3-dioxolane. This was stirred in 20 mL of 1M HCl for 40 hours. The mixture was neutralized with sodium bicarbonate and extracted with 100 mL of dichloromethane. The dichloromethane extract was dried over magnesium sulfate and evaporated to yield 2.5 g of the desired aldehyde as an oil.

Provenance & Evidence