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The Journal of Organic Chemistry

The Journal of Organic Chemistry

IF: 3.3
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Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids with 1-Hydroxycyclohexyl Phenyl Ketone

Published:22 June 2023 DOI: 10.1021/acs.joc.3c00096 PMID: 37348118
Yi Lu, Wen-Yun Tan, Yuzhen Ding, Wen Chen and Hongbin Zhang*, 

Abstract

The oxidation of primary alcohols to the corresponding carboxylic acids is one of the fundamental and useful reactions in organic synthesis. In this paper, we report our comprehensive results toward the oxidation of primary alcohols and aldehydes to acids via hydride transfer reactions mediated by 1-hydroxycyclohexyl phenyl ketone. Under the strong basic conditions of sodium tert-butoxide, the room temperature oxidations tolerate a range of functional groups, including vulnerable tert-butanesulfinamides, amines, sulfides, olefins, and heterocycles, and provide good to excellent yields. Most importantly, our oxidation procedure can be applied to chemoselective oxidation of primary alcohols and aldehydes to carboxylic acids in the presence of secondary alcohols.

Substances (2)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Sodium tert-butoxide 865-48-5 C4H9NaO 723 suppliers $11.20-$2501.30
1-Hydroxycyclohexyl phenyl ketone 947-19-3 C13H16O2 521 suppliers $5.00-$2467.08

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