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Preparation and selective hydrolysis of acetal esters
Author(s) -
Adlof R. O.,
Neff W. E.,
Emken E. A.,
Pryde E. H.
Publication year - 1977
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02671022
Subject(s) - acetal , chemistry , ozonolysis , hydrolysis , ozonide , aldehyde , decomposition , organic chemistry , gas chromatography , chromatography , catalysis
and Summary Medium chain length aldehydic acids and esters (C 8 ‐C 13 ) 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 CH 3 OH‐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 H 2 O‐HC1‐CH 3 CN 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.