Ozonolysis of Olefins, II1; Linseed Oil as a Renewable Resource for Alkyl 3,3-Dialkoxypropanoates

Martin Mittelbach; Norbert Poklukar

doi:10.1055/s-1990-26868

Synthesis 1990; 1990(4): 331-332
DOI: 10.1055/s-1990-26868

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Ozonolysis of Olefins, II¹; Linseed Oil as a Renewable Resource for Alkyl 3,3-Dialkoxypropanoates

Martin Mittelbach^* , Norbert Poklukar

^*Institute for Organic Chemistry, Karl-Franzens-Universität, Graz, Heinrichstraße 28, A-8010 Graz, Austria

Abstract

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A new approach to the synthesis of alkyl 3,3-dialkoxypropanoates, which are important intermediates in organic synthesis, starting from fatty acid esters is described. Thus, ozonolysis of methyl linoleate and methyl linolenate in alcoholic hydrogen chloride affords a reaction mixture, from out of which the alkyl 3,3-dialkoxypropanoates can be isolated by fractional distillation in 60-65% yield. Even linseed oil, which contains high amounts of linolic and linolenic acid, can be used as starting material, after conversion into the methyl esters by methanolysis. Byproducts of the ozonolysis can be oxidized to the corresponding carboxylic acids which are valuable intermediates in oleochemistry.

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