Ozonolysis of olefins, VI: Cyanoacetaldehyde by ozonolysis of (E)-1,4-dicyano-2-butene or allyl cyanide

Article abstract of DOI:10.1055/s-1992-26088

A new route for the preparation of cyanoacetaldehyde (3-oxopropanenitrile, 1) and its stable dimethyl acetal (3,3-dimethoxypropanenitrile, 2), which both are valuable intermediates for organic syntheses, is described. It starts from (E)-1,4-dicyano-2-butene or allyl cyanide (3-butenenitrile), respectively, which are ozonized at -40°C and further treated with dimethyl sulfide to give a solution of 1. This solution can either be used directly for further reactions or be transformed into the dimethyl acetal 2. The overall yield of 2 is 67 to 71%. The acetal can be hydrolyzed again by treatment with Amberlyst-15 to give 1.