OXIDATIVE ESTERIFICATION OF BENZALDEHYDE AND DEACTIVATED AROMATIC ALDEHYDES WITH N-BROMOSUCCINIMIDE-PYRIDINE

被引：16

作者：

Agrawal, Manoj K. ^{[1
]}

Adimurthy, Subbarayappa ^{[1
]}

Ghosh, Pushpito K. ^{[1
]}

机构：

[1] Cent Salt & Marine Chem Res Inst, Council Sci & Ind Res, Bhavnagar 364002, Gujarat, India

来源：

SYNTHETIC COMMUNICATIONS | 2012年 / 42卷 / 19期

关键词：

Benzaldehydes; esterification; methyl benzoates; NBS; oxidation; BENZYLIC ALCOHOLS; ACTIVATED CARBOXYLATES; CATALYTIC GENERATION; DIRECT CONVERSION; METHYL-ESTERS; REAGENT; IODINE; VERSATILE; BROMINE; ACID;

D O I：

10.1080/00397911.2011.572219

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (R) to view the free supplemental file.

引用

页码：2931 / 2936

页数：6

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