Water → 2-Methyl-4-(2-oxoethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-cyano-3-methylphenyl)oxirane-2-carboxylate (927 mg, 4.0 mmol) in 5 mL of dry ethanol was cooled to 0° C. Freshly prepared EtONa (5 mmol) in 4 mL of ethanol was added and stirred at 0° C. for 10 min. Then dropwise addition of 0.1 g of water, stirred at 0° C. for 2 hours, and the sodium salt of the epoxy compound was filtered. The sodium salt of the epoxy compound was then dissolved in 5 mL of water and added 5 mL of 1 N of HCl and 20 mL of toluene. The mixture was heated to reflux for 2 hours. The organic phase was separated, washed by saturated sodium chloride, dried over Na2SO4 and distilled off solvent to afford crude 2-methyl-4-(2-oxoethyl)benzonitrile. MS m/z: 160 (M+1)+.

Provenance & Evidence