One step conversion of tert-butyl ester to corresponding acyl chloride by thionyl chloride using water-free acetonitrile as solvent

A novel one-step protocol for the preparation of acyl chlorides directly from tert -butyl esters is described. The method employs anhydrous acetonitrile as the reaction medium and thionyl chloride (SOCl₂) as the chlorinating agent, facilitating the transformation under mild conditions to afford the target products in nearly quantitative yields. The reaction exhibits broad substrate scope, delivering excellent yields across a range of substrates. Notably, the simplicity, operational efficiency, and inherent safety of this procedure position it as a compelling alternative to existing methods for the synthesis of acyl chloride. A mechanism involving a Ritter-driven pathway is proposed to rationalize the conversion.

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Publication Details

Journal
Tetrahedron Letters
Published
2026-06-30
DOI
https://doi.org/10.1016/j.tetlet.2026.156195
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
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article

One step conversion of tert-butyl ester to corresponding acyl chloride by thionyl chloride using water-free acetonitrile as solvent

Ailin Shan, Shuai Song, Xiaozhou Zhang, Jiaqiang Cai et al.
Tetrahedron Letters
Sulfur-Based Synthesis Techniques
article

One step conversion of tert-butyl ester to corresponding acyl chloride by thionyl chloride using water-free acetonitrile as solvent

Ailin Shan, Shuai Song, Xiaozhou Zhang, Jiaqiang Cai, Yaoxu Hong, Zizhen Wang, Lixia Zhang, Tongtong Xue
article en

Abstract

A novel one-step protocol for the preparation of acyl chlorides directly from tert -butyl esters is described. The method employs anhydrous acetonitrile as the reaction medium and thionyl chloride (SOCl₂) as the chlorinating agent, facilitating the transformation under mild conditions to afford the target products in nearly quantitative yields. The reaction exhibits broad substrate scope, delivering excellent yields across a range of substrates. Notably, the simplicity, operational efficiency, and inherent safety of this procedure position it as a compelling alternative to existing methods for the synthesis of acyl chloride. A mechanism involving a Ritter-driven pathway is proposed to rationalize the conversion.

Tetrahedron LettersVol. 183
Suzhou Research Institute (CN)
Clean water and sanitation
Openalex Percentile: Top 14%
Sulfur-Based Synthesis Techniques
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