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Citation: JIAO Yan, FANG Zhi-Jie, JIANG Yu-Hua, ZHENG Bao-Hui. A Novel Synthetic Method for 2,2',4,4'-Tetra Carboxylic Acid Biphenyl[J]. Chinese Journal of Applied Chemistry, ;2007, 24(7): 844-846. shu

A Novel Synthetic Method for 2,2',4,4'-Tetra Carboxylic Acid Biphenyl

1.
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: FANG Zhi-Jie,
Received Date: 27 July 2006
Available Online: 25 September 2006

A novel method for the synthesis of 2,2',4,4'-tetra carboxylic acid biphenyl with p-methyl aniline as raw material is described in this article.Firstly,2-amino-5-methylbenzoic acid was prepared from p-methyl aniline in three steps with a yield of 61.5%.The process was optimized and the quantities of the reactants were reduced remarkably.Then,4,4'-dimethyl-2,2'-diphenylic acid was obtained by the coupling of diazonium which was made by the diazotization of 2-amino-5-methylbenzoic acid.The effect of molar ratio of NaOH to NH₂OH·HCl on the yield was researched.It was found that the maximum yield of 4,4'-dimethyl-2,2'-diphenylic acid was 88% when the molar ratio was 1:1.Finally,the target product 2,2',4,4'-tetra carboxylic acid biphenyl was prepared from the oxidation of 4,4'-dimethyl-2,2'-diphenylic acid by KMnO₄ in an alkaline solution.Total yield based on p-methyl aniline was 43.3%.The structure of the product was characterized by ¹H NMR and IR (KBr).By using benzoic diazonium as a reactant,this synthetic route for tetra carboxylic biphenyl uses mild reaction condition,with high yields and good industrial application potential.
- aminomethyl benzoic acid,
- tetra carboxylic acid biphenyl,
- synthesis,
- coupling,
- diazonium
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