Conversion of aromatic methyl ketones to esters and carboxylic acids using <i>o</i> -phthalaldehyde as an oxidant

Herein we describe a two-step conversion of aromatic methyl ketones to esters and carboxylic acids employing <i>o</i>-phthalaldehyde as an oxidant. In the first step, <i>o</i>-phthalaldehyde oxidizes the methyl group to 1-indanone, which acts as a leaving group in a subsequent regioselective retro-Claisen condensation to form esters and carboxylic acids. The mild oxidation conditions ensure the method is applicable to a broad range of substrates. Additionally, the two-step method is operationally simple and scalable, and can also be performed in a single pot.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-12-03
DOI
https://doi.org/10.1039/d4ob01933d
Citations
1
Primary Topic
Chemical Synthesis and Reactions
Type
article
Field-Weighted Citation Impact
0.25
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article

Conversion of aromatic methyl ketones to esters and carboxylic acids using o -phthalaldehyde as an oxidant

R. Maity, Partha Ghosh, Saurabh Kumar Singh, Rajendra Prasad
1 citations
Organic & Biomolecular Chemistry
Chemical Synthesis and Reactions
0.25
article

Conversion of aromatic methyl ketones to esters and carboxylic acids using o -phthalaldehyde as an oxidant

R. Maity, Partha Ghosh, Saurabh Kumar Singh, Rajendra Prasad
article en
1 citations

Abstract

Herein we describe a two-step conversion of aromatic methyl ketones to esters and carboxylic acids employing <i>o</i>-phthalaldehyde as an oxidant. In the first step, <i>o</i>-phthalaldehyde oxidizes the methyl group to 1-indanone, which acts as a leaving group in a subsequent regioselective retro-Claisen condensation to form esters and carboxylic acids. The mild oxidation conditions ensure the method is applicable to a broad range of substrates. Additionally, the two-step method is operationally simple and scalable, and can also be performed in a single pot.

Organic & Biomolecular ChemistryVol. 23(5)
Central University of Jharkhand (IN)
Openalex Percentile: Top 46%
Chemical Synthesis and Reactions
0.25
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