Selective and Efficient Oxidation of Benzylic Alcohols to Benzaldehydes and Methyl Benzoates by Dibromo-5,5-dimethylhydantoin

被引：8

作者：

Li, Zhongzhou ^{[1
]}

Zhu, Wei ^{[1
]}

Bao, Jinlong ^{[1
]}

Zou, Xinzhuo ^{[1
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai 200241, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 08期

关键词：

methyl benzoate; Benzaldehyde; oxidation; dibromo-5,5-dimethylhydantoin; chemoselective; AEROBIC OXIDATION; CATALYZED OXIDATION; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; ALDEHYDES; KETONES; GREEN; ACETOPHENONES; ESTERS; ACID;

D O I：

10.1080/00397911.2013.856447

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selective and efficient method of oxidizing benzyl alcohols to benzaldehydes and methyl benzoates by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as oxidant is developed. One-step conversion of benzyl alcohols to methyl benzoates in methanol at room temperature for 12 hours is achieved without any catalysts. Moreover, para-substituted benzyl alcohols are obtained in 86-98% yield. When dichloromethane is used as solvent, further oxidation of benzaldehydes to esters is well controlled, selectively affording benzaldehydes in 89-99% yield within 30 minutes. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

引用

页码：1155 / 1164

页数：10

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