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林产化学与工业 ›› 2021, Vol. 41 ›› Issue (1): 15-20.doi: 10.3969/j.issn.0253-2417.2021.01.003

• 重点研发专栏 • 上一篇    下一篇

利用1, 2, 3-三甲氧基苯合成2, 3, 4, 4'-四羟基二苯甲酮

刘兰香1, 黄维东1,2, 董刚1,3, 李坤1, 马金菊1, 张弘1,*()   

  1. 1. 中国林业科学研究院 资源昆虫研究所, 云南 昆明 650224
    2. 西南林业大学 化学化工学院, 云南 昆明 650228
    3. 昆明理工大学 化学工程学院, 云南 昆明 650500
  • 收稿日期:2020-08-28 出版日期:2021-02-28 发布日期:2021-03-03
  • 通讯作者: 张弘 E-mail:kmzhhong@163.com
  • 作者简介:张弘, 研究员, 研究领域为林产化学; E-mail: kmzhhong@163.com
    刘兰香(1986-), 女, 云南普洱人, 助理研究员, 硕士, 研究方向为林产化学
  • 基金资助:
    国家重点研发计划资助项目(2018YFD0600404)

Synthesis of 2, 3, 4, 4'-Tetrahydroxybenzophenone from 1, 2, 3-Trimethoxybenzene

Lanxiang LIU1, Weidong HUANG1,2, Gang DONG1,3, Kun LI1, Jinju MA1, Hong ZHANG1,*()   

  1. 1. Research Institute of Resources Insects, Chinese Academy of Forestry, Kunming 650224, China
    2. Faculty of Chemical Engineering, Kunming University of Science and Technology, Kunming 650228, China
    3. Faculty of Chemical Engineering, Kunming University of Science and Technology, Kunming 650500, China
  • Received:2020-08-28 Online:2021-02-28 Published:2021-03-03
  • Contact: Hong ZHANG E-mail:kmzhhong@163.com

摘要:

为解决2,3,4,4'-四羟基二苯甲酮(4HBP)的传统合成方法中原料易氧化的问题,采用羟基保护方法,以1,2,3-三甲氧基苯(TMB)和对甲氧基苯甲酸(p-AA)为原料、伊顿试剂为催化剂,1,2-二氯乙烷为溶剂,首次合成重要的中间体化合物2,3,4,4'-四甲氧基二苯甲酮(4TMP),然后在BBr3/CH2Cl2体系、无水无氧、低温的条件下,将4TMP进行脱甲基反应高效合成了目标产物4HBP,目标产物收率约为86.4%,纯度≥97.59%,各金属离子均小于18.60 mg/kg。通过红外光谱、核磁共振谱、质谱等方法确证了中间产物和目标产物的结构。

关键词: 羟基保护, 2, 3, 4, 4'-四羟基二苯甲酮, 2, 3, 4, 4'-四甲氧基二苯甲酮, 伊顿试剂

Abstract:

To prevent the oxidation of raw materials(pyrogallic acid and p-hydroxybenzoic acid)during the traditional synthesis of 2, 3, 4, 4'-tetrahydroxybenzophenone(4HBP), an intermediate compound, 2, 3, 4, 4'-tetramethoxydibenzone(4TMP), was synthesized for the first time by the hydroxyl protection method. 1, 2, 3-trimethoxybenzene(TMB) and p-anisic acid(p-AA) were used as the raw materials, and Eaton reagent and 1, 2-dichloroethane were used as the catalyst and solvent, respectively. The target product, 2, 3, 4, 4'-tetrahydroxybenzophenone, was synthesized by demethylation of the intermediate in a BBr3/CH2Cl2 system with anhydrous, anaerobic and low temperature conditions. The yield of the target product was approximately 86.4%, and the purity was ≥98.8%, the content of each metal ion was less than 18.60 mg/kg.The structures of the intermediate and target products were investigated by IR, NMR, and MS.

Key words: hydroxyl protection, 2, 3, 4, 4'-tetrahydroxybenzophenone, 2, 3, 4, 4'-tetramethoxybenzophenone, Eaton reagent

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