Omega-formylalkanoates by ozonization of unsaturated fatty esters

Ozonization of the methyl esters of 11-eicosenoic, linoleic, erucic and linolenic acids gave a number of different homologous methyl ω-formylalkanoates. Complete ozonization of the monounsaturated esters formed C₁₁ and C₁₃ compounds with 90% conversion; partial ozonization of the polyunsaturated esters gave C₁₂ and C₁₅ products with maximum conversions at ca. 75% consumption of fatty ester. Thus, methyl linoleate gave 52 and 23% conversions to the 9- and 12-carbon products, and methyl linolenate gave 29, 27 and 19% conversions to the 9-, 12- and 15-carbon products. Yields of aldehyde or acetal esters in distilled products were 70–90% in preparative-scale experiments. Kinetic analysis showed that ozone attack was essentially random. Methanol was used as a participating solvent. Presented in part at the AOCS Meeting, New Orleans, 1962. A laboratory of the No. Util. Res. & Dev. Div., ARS, USDA.