Collect. Czech. Chem. Commun. 1988, 53, 822-832

Reaction of 4-substituted benzaldehydes and acetophenones with chloroacetonitrile

Jiří Svoboda, Zuzana Kocfeldová and Jaroslav Paleček

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


Under conditions of phase-transfer catalysis or in homogeneous solution of potassium tert-butoxide the title compounds give stereoisomeric mixtures of substituted 2,3-epoxy nitriles III and IV. Alkaline hydrolysis of epoxy nitriles IV afforded the corresponding 2-arylpropanals in low yields. On treatment with methanol and potassium carbonate, epoxy nitriles III and IV were converted into epoxy esters in good yields.