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 ३‐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舑90% in preparative‐scale experiments. Kinetic analysis showed that ozone attack was essentially random. Methanol was used as a participating solvent.