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Abstract <p>The synthesis and rearrangement reactions of 2-methoxyphenyl chloroacetate in the presence of low amounts of catalysts to form <i>o</i>- and <i>p-</i>hydroxy-3-methoxyphenacyl chlorides are described in this study. A method for obtaining <i>m</i>-methoxyphenyl chloroacetate is developed, based on the chloroacetylation of <i>m</i>‑methoxyphenol in benzene solution.. The reactions of <i>m</i>-methoxyphenyl chloroacetate are rearranged for the first time in the presence of low amounts of FeCl<sub>3</sub>, MoCl<sub>5</sub>, WCl<sub>6</sub>, ZnCl<sub>2</sub>, SnCl<sub>4</sub>, VCl<sub>3</sub>, FeCl<sub>3</sub>⋅6H<sub>2</sub>O, Fe<sub>2</sub>(SO<sub>4</sub>)<sub>3</sub>, iron acetylacetonate (IAA), and iron salicylate (ISA). The reaction leads to the formation of 2‑hydroxy-4-methoxyphenacyl chlorides and 4-hydroxy-2-methoxyphenacyl chlorides. The percentage ratio of isomers depends on the reaction conditions. The synthesis of 4-methoxyphenyl chloroacetate via reaction with diphenylthiocarbazone in the presence of dimethylformamide is studied. The structure of the substances is elucidated with UV, IR, and NMR spectroscopies.</p>

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Chloroacetylation of Substituted Methoxyphenols: Synthesis and Subsequent Transformations

  • 期刊论文

  • 发表日期：

    2025年9月4日

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  • A. U. Choriev,
  • A. K. Abdushukurov

摘要

Abstract

The synthesis and rearrangement reactions of 2-methoxyphenyl chloroacetate in the presence of low amounts of catalysts to form o- and p-hydroxy-3-methoxyphenacyl chlorides are described in this study. A method for obtaining m-methoxyphenyl chloroacetate is developed, based on the chloroacetylation of m‑methoxyphenol in benzene solution.. The reactions of m-methoxyphenyl chloroacetate are rearranged for the first time in the presence of low amounts of FeCl3, MoCl5, WCl6, ZnCl2, SnCl4, VCl3, FeCl3⋅6H2O, Fe2(SO4)3, iron acetylacetonate (IAA), and iron salicylate (ISA). The reaction leads to the formation of 2‑hydroxy-4-methoxyphenacyl chlorides and 4-hydroxy-2-methoxyphenacyl chlorides. The percentage ratio of isomers depends on the reaction conditions. The synthesis of 4-methoxyphenyl chloroacetate via reaction with diphenylthiocarbazone in the presence of dimethylformamide is studied. The structure of the substances is elucidated with UV, IR, and NMR spectroscopies.