Gordon G. Moore

Enol esters XVI: Enol ethers in synthesis

The synthesis of isopropenyl octadecyl ether is reported. This compound is a useful reagent for the synthesis of wax esters by reaction with long chain fatty acids, and of symmetrical or unsymmetrical ethers via reaction with long chain alcohols. The long chain alkyl isopropenyl ether is more sensitive to hydrolysis than the corresponding enol ester and forms successively the ketal 2,2-dioctadecyloxypropane, and octadecanol and acetone. Glycerol reacts with propyne yielding glycerol acetonide, glycerol acetonide isopropenyl ether and diglycerol bisacetonide. New crystalline derivatives of diglycerol are described, useful for the characterization of that substance.