Potassium Cyanide → 3-(2-Chlorophenyl)-3-hydroxypropanenitrile

Participants

Reaction Conditions

Reaction Steps

2-(2-chloro-phenyl)-oxirane (440 mg, 2.85 mmol) was dissolved in ethanol (3 mL) and treated with potassium cyanide in water (3 mL) and hydrogen chloride (4 M in 1,4-dioxane, 0.71 mL) subsequently. The mixture was stirred at 50° C. for 8 hr and room temperature for overnight. Saturated sodium hydrogen carbonate was added and the mixture was concentrated. The residue was extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (40 g silica gel cartridge) eluting with ethyl acetate/hexane (0%-30%) to give the product as a colorless oil (330 mg, 64%). 1H NMR (CDCl3) δ 7.70-7.60 (m, 1H), 7.40-7.20 (m, 2H), 5.50-5.40 (m, 1H), 2.98-2.85 (m, 1H), 2.85-2.80 (m, 1H), 2.78-2.65 (m, 1H).

Provenance & Evidence