The reaction of aspirin with base

Sosale Chandrasekhar, Honnaiah Vijay Kumar

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


Aspirin anion appears to exist only fleetingly, rearranging via acetyl transfer to the ortho carboxylate group, as indicated by IR, UV and NMR. The resulting mixed anhydride cyclises to the more stable bicyclic orthoacetate isomer, a process facilitated by time and increasing pH. Mechanistic possibilities are discussed to explain these intriguing observations.

Original languageEnglish (US)
Pages (from-to)3561-3564
Number of pages4
JournalTetrahedron Letters
Issue number28
StatePublished - Jul 13 2011

Bibliographical note

Funding Information:
We thank University Grants Commission (New Delhi) for a D. S. Kothari postdoctoral fellowship to H.V.K. We also remain grateful to a referee for several constructive suggestions which led to a vastly improved manuscript.

Copyright 2011 Elsevier B.V., All rights reserved.

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