Tetrahedron p. 2471 - 2476 (1988)
Update date:2022-08-30
Topics:
Plusquellec, Daniel
Roulleau, Fabienne
Lefeuvre, Martine
Brown, Eric
Acyl chlorides and alkylchloroformates smoothly reacted with one molar equivalent of sodium hydroxide, using liquid-liquid phase transfer conditions to afford high yields of the corresponding symmetrical carboxylic and carbonic hemiester anhydrides.Unstable anhydrides such as 4-nitrobenzoic, 2-furoic and methacrylic anhydrides, which are otherwise difficult to obtain, were easily prepared by this method.The reaction mechanism does not seem to involve intermediate hydrolysis of half the acid chloride into the corresponding sodium carboxylate.
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