Synthesis of novel γ-ketoesters from succinic anhydride

Article abstract of DOI:10.14233/ajchem.2013.15179

Four alkyl g-ketohexanoates (3a-3d) have been prepared from succinic anhydride employing a three step reaction strategy. In the first step using p-toluene sulfonic acid as catalyst, the ring of succinic anhydride was opened with isopropyl, isobutyl, isopentyl and benzyl alcohols, respectively to form alkyl hydrogen succinates (1a-1d). In the 2nd step these alkyl hydrogen succinates on treatment with SOCl2 yielded 4-alkoxy-4-ketobutanoyl chlorides (2a-2d). The acid halides thus obtained, on reaction with diethyl cadmium led to require g-ketoesters. All the synthesised compounds were characterized by recording and analyzing 1H, 13C NMR, IR spectra and mass measurements.