{"title":"取代甲氧基苯酚的氯乙酰化：合成和随后的转化","authors":"A. U. Choriev, A. K. Abdushukurov","doi":"10.3103/S002713142570035X","DOIUrl":null,"url":null,"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>","PeriodicalId":709,"journal":{"name":"Moscow University Chemistry Bulletin","volume":"80 5","pages":"321 - 329"},"PeriodicalIF":0.5000,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chloroacetylation of Substituted Methoxyphenols: Synthesis and Subsequent Transformations\",\"authors\":\"A. U. Choriev, A. K. Abdushukurov\",\"doi\":\"10.3103/S002713142570035X\",\"DOIUrl\":null,\"url\":null,\"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>\",\"PeriodicalId\":709,\"journal\":{\"name\":\"Moscow University Chemistry Bulletin\",\"volume\":\"80 5\",\"pages\":\"321 - 329\"},\"PeriodicalIF\":0.5000,\"publicationDate\":\"2025-09-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Moscow University Chemistry Bulletin\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://link.springer.com/article/10.3103/S002713142570035X\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Moscow University Chemistry Bulletin","FirstCategoryId":"1085","ListUrlMain":"https://link.springer.com/article/10.3103/S002713142570035X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Chloroacetylation of Substituted Methoxyphenols: Synthesis and Subsequent Transformations
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.
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.
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