13-aminotridecanoic Acid from Erucic Acid

13-Aminotridecanoic acid, the monomer for nylon 13, was synthesized from commercial erucic acid or its derivatives by several methods in a study to determine the method of choice, which involved oxidative ozonolysis of eruconitrile, followed by esterification before isolation to give methyl 12-cyanododecanoate. The cyano ester was then catalytically reduced and hydrolyzed, without isolation of intermediates, to give very pure 13-aminotridecanoic acid in 55 to 60% yield from the eruconitrile. Almost equally convenient was a method starting with oxidative ozonolysis of methyl erucate to the half ester of brassylic acid, which was then converted successively to the amide-ester, nitrile-ester, amino ester, and amino acid. Other methods tried were significantly less desirable because of low yields and difficult purifications.