Diels-alder reactions of 2-methoxy-1,3-butadiene

Abstract

Conditions have been found under which 2-methoxy-1,3-butadiene reacts with maleic anhydride and citraconic anhydride to form Diels-Alder adducts in almost quantitative yields. The condensation of this diene with ethyl 2-butynoate occurs less rapidly and in somewhat poorer yield to produce an adduct which on mild acid hydrolysis affords Hagemann’s ester. Thus, a new route to Hagemann’s ester and related compounds is at hand. © 1952, American Chemical Society. All rights reserved.