Preparation and selective hydrolysis of acetal esters

Abstract and Summary Medium chain length aldehydic acids and esters (C8‐C13) were synthesized by ozonolysis of readily available cyclic and straight chain alkenoate esters followed by rearrangement or reduction of the ozonide. The acetal esters, prepared by reaction of the aldehydic acids with CH3OH‐HC1, were characterized by gas liquid chromatography, proton magnetic resonance, carbon magnetic resonance, thin layer chromatography, and infrared analysis. Selective hydrolysis of the acetal esters to aldehyde esters was conveniently accomplished with H2O‐HC1‐CH3CN to give 95% or higher yields in less than 30 min. Development of this simple and effective hydrolysis procedure allows these medium chain length esters to be safely stored as their acetal esters, which retards their oxidation, trimerization, and decomposition.