Synthetic Communications p. 2931 - 2936 (2012)
Update date:2022-08-18
Topics:
Agrawal, Manoj K.
Adimurthy, Subbarayappa
Ghosh, Pushpito K.
(Chemical Equation Presented) Whereas the oxidative esterification of benzaldehyde to methyl benzoate with N-bromosuccinimide (NBS)-pyridine requires dark conditions and 5 equivalents each of NBS and K2CO3 and gave only moderate yield (52%) of the product (McDonald et al. J. Org. Chem. 1989, 54, 1213), simple change of base to pyridine gave the desired product in 83% gas chromatographic yield with only 1 equivalent each of NBS and pyridine. Moreover, the reaction could be conducted without exclusion of light. Aromatic aldehydes bearing electron-withdrawing substituents at meta/para position yielded the corresponding methyl esters in still better yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
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