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Chemistry and Industry of Forest Products ›› 2021, Vol. 41 ›› Issue (1): 15-20.doi: 10.3969/j.issn.0253-2417.2021.01.003

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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


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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