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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (05): 561-566. 上一篇    下一篇

研究论文

2-甲基-4-甲氧基苯基苯胺的合成

邱潇1，姜佳俊2，王幸宜2，沈永嘉*,1   

  1. (1华东理工大学结构可控先进功能材料及其制备教育部重点实验室和精细化工研究所 上海 200237)
    (2华东理工大学化学系 上海 200237)
  • 收稿日期:2004-09-06 修回日期:2004-11-24 发布日期:2004-04-30
  • 通讯作者: 沈永嘉

Synthesis of N-Phenyl-2-methyl-4-methoxyaniline

QIU Xiao1,JIANG Jia-Jun2,WANG Xing-Yi2, SHEN Yong-Jia*,1   

  1. (1 Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Sci-ence and Technology, Shanghai 200237)
    (2 Department of Chemistry, East China University of Science and Technology, Shanghai 200237)
  • Received:2004-09-06 Revised:2004-11-24 Published:2004-04-30
  • Contact: SHEN Yong-Jia

PDF

2936

被引次数

6

邻硝基甲苯在甲醇、乙酸和硫酸混合溶液中, 在Pt/C的催化下发生氢化和Bamberger重排生成2-甲基-4-甲氧基苯胺. 后者在Pd/C的存在下以苯酚为反应介质与环已酮缩合生成2-甲基-4-甲氧基苯基苯胺, 反应总产率63.0%. 文中给出了产物与中间产物的核磁共振氢谱和质谱, 同时讨论了影响反应的因素.

关键词: 邻硝基甲苯, Bamberger重排, 合成, 2-甲基-4-甲氧基苯基苯胺

Using Pt/C as a catalyst, the hydrogenation and Bamberger rearrangement of o-nitrotoluene was carried out in a solution consisting of methanol, sulfuric acid and acetic acid, to afford 2-methyl-4-meth- oxyaniline. The intermediate product was further reacted with cyclohexanone in the presence of Pd/C in phenol to form N-phenyl-2-methyl-4-methoxyaniline. The total yield is 63%. The product as well as intermediate was determined by 1H NMR and MS spectra. The factors of affecting the reactions were also discussed.

Key words: synthesis, Bamberger rearrangement, N-phenyl 2-methyl-4-methoxyaniline, o-nitrotoluene