Base-Induced Alcoholysis ofN-Arylmaleimides: Facile in situ Oxa-Michael Additionto Alkyl Maleanilates: Two-Step One-Pot Rapid Access to AlkoxysuccinicAcids

Abstract

A simple, efficient and general two-step, one-pot approach to alkoxysuccinic acids is described. The potassium carbonate-catalyzed reactions of alcohols with N-p-tolylmaleimide (4) followed by an acid-induced hydrolysis of intermediate products furnished alkoxysuccinic acids 1a-f in 90-98% yields. All the intermediates from the reaction of imide 4 with alcohols have been isolated and characterized, proving that the in situ formed alkyl maleanilates 3 are the actual Michael acceptors. a The mixture of 5g, 6g/h and 7g/h on acid-catalyzed hydrolysis furnished malic acid with 85% yield and not the expected 1g/h.