Alcohols from ozonolysis products of unsaturated fatty esters

1-Nonanol and alkyl 9-hydroxynonanoates were more readily prepared by hydrogenation of the respective isolated aldehydes than by direct hydrogenation of products from reductive ozonolysis of oleate esters. Hydrogenation with nickel catalysts and aprotic solvents reduced the isolated aldehydes in good yield with a minimum of side reactions. Although the noble metal catalyst and hydroxylic solvent systems frequently used in similar reductions were also effective, they required a promoter that fortuitously catalyzed hydrolysis of acetals that formed during hydrogenation. Direct hydrogenation of the ozonolysis products resulted in side reactions and a mixture of products difficult to separate. Presented in part at the AOCS meeting, Chicago, October 1967.