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Synthesis 1992; 1992(3): 275-276
DOI: 10.1055/s-1992-26088
short paper
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Ozonolysis of Olefins, VI:1 Cyanoacetaldehyde by Ozonolysis of (E)-1,4-Dicyano-2-butene or Allyl Cyanide

Madhukar Jachak* , Martin Mittelbach, Ulrike Krießmann, Hans Junek
  • *Institute for Organic Chemistry, Karl-Franzens-Universität, Graz, Heinrichstraße 28, A-8010 Graz, Austria
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Publication Date:
17 September 2002 (online)

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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.