Synthesis of 6-bromohexanol from ε-caprolactone: synthetic features and theoretical aspects

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2025-05-15 DOI:10.1007/s11172-025-4595-5

A. D. Trubachev, K. V. Zaitsev

引用次数: 0

Abstract

A three-steps procedure for obtaining 6-bromohexanol from available ε-caprolactone was modified to reach a total yield of 43%. Quantum chemistry methods were used to study a side process occurring in the second step of the synthesis, namely, the esterification of Br(CH₂)₅COOH with methanol which gives MeO(CH₂)₅COOMe, and a mechanism for the implementation of this step was proposed. Based on the suggested mechanism, the procedure for performing this step was corrected to avoid the side product formation.

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ε-己内酯合成6-溴己醇：合成特点及理论研究

对现有ε-己内酯制备6-溴己醇的三步法进行了改进，使总收率达到43%。利用量子化学方法研究了合成第二步中Br(CH2)5COOH与甲醇酯化反应生成MeO(CH2)5COOMe的副过程，并提出了该步骤的实现机理。基于建议的机制，执行这一步的程序被纠正以避免副产物的形成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.