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›› 2013, Vol. 33 ›› Issue (4): 93-100.doi: 10.3969/j.issn.0253-2417.2013.04.018

• 1研究报告 • Previous Articles     Next Articles

Synthesis of 3,4,5-Trimethoxyaniline

XU Xu1,2, LIU Bing1, YANG Yang1, WANG Shi-fa1,2   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;2. Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, Nanjing 210037, China
  • Received:2012-08-13 Revised:1900-01-01 Online:2013-08-30 Published:2013-08-30

Abstract: 3,4,5-trimethoxyaniline was synthesized from 3,4,5-trimethoxybenzioc acid. 3,4,5-trimethoxyaniline through chlorination of 3,4,5-trimethoxybenzioc acid, amidation of 3,4,5-trimethoxybenzoyl chloride and Hofmann rearrangement reaction of 3,4,5-trimethoxybenzamide. The structure of 3,4,5-trimethoxyaniline was determined by FT-IR and GC-MS spectra. The optimal reaction conditions of 3,4,5-trimethoxybenzoyl chloride was as follows: n(phosphorus trichloride):n(3,4,5-trimethoxybenzioc acid)=0.65:1, toluene as the solvent, v(toluene):n(3,4,5-trimethoxybenzioc acid)=0.6:1(L:mol), reaction temperature 80℃, reaction time 3 h. The optimal reaction conditions of (3,4,5-trimethoxybenzamide) was as follows: n(ammonia):n(3,4,5-trimethoxybenzoyl chloride)=4:1, reaction temperature-5-0℃, reaction time 30 min. The optimal reaction conditions of (3,4,5-trimethoxyaniline) was as follows: n(NaOH):n(3,4,5-trimethoxybenzamide)=9:1, n(Br2):n(3,4,5-trimethoxybenzamide)=1.15:1, rearrangement reaction temperature 40℃, rearrangement reaction time 20 min, decarboxylation temperature 85℃, decarboxylation time 1 h, deionized water as the solvent. Yield of obtained product was 66.8%, m.p. 112.5-113.5℃, purity of obtained product was 99.0%.

Key words: 5-trimethoxybenzoic acid, Hofamnn rearrangement, 5-trimethoxyaniline

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