Chloroacetylation of Substituted Methoxyphenols: Synthesis and Subsequent Transformations

IF 0.5 Q4 CHEMISTRY, MULTIDISCIPLINARY

Moscow University Chemistry Bulletin Pub Date : 2025-09-04 DOI:10.3103/S002713142570035X

A. U. Choriev, A. K. Abdushukurov

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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.

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取代甲氧基苯酚的氯乙酰化：合成和随后的转化

本研究描述了在少量催化剂作用下2-甲氧基苯基氯乙酸酯的合成和重排反应，生成o-和对羟基-3-甲氧基苯基氯化物。以间甲氧基苯酚在苯溶液中的氯乙酰化反应为基础，提出了间甲氧基苯氯乙酸酯的制备方法。在少量FeCl3、MoCl5、WCl6、ZnCl2、SnCl4、VCl3、FeCl3⋅6H2O、Fe2(SO4)3、乙酰丙酮铁（IAA）和水杨酸铁（ISA）的存在下，间甲氧基苯基氯乙酸酯的反应首次发生了重排。该反应生成2-羟基-4-甲氧基苯酰氯和4-羟基-2-甲氧基苯酰氯。同分异构体的百分率取决于反应条件。研究了在二甲基甲酰胺存在下，与二苯硫脲反应合成4-甲氧基苯基氯乙酸酯。用紫外、红外和核磁共振光谱分析了物质的结构。

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来源期刊

Moscow University Chemistry Bulletin CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

1.30

自引率

14.30%

发文量

期刊介绍： Moscow University Chemistry Bulletin is a journal that publishes review articles, original research articles, and short communications on various areas of basic and applied research in chemistry, including medical chemistry and pharmacology.