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Synthesis 1995; 1995(1): 41-43
DOI: 10.1055/s-1995-3851
short paper
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Practical Synthesis of 4’-Methylbiphenyl-2-carboxylic Acid

Tetsutaro Hattori1 , Noriyuki Hayashizaka2 , Sotaro Miyano1
  • 1Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University, Aramaki-Aoba, Aoba-ku, Sendai 980-77, Japan
  • 2Sumitomo Seika Chemicals Co., Ltd., 346-1, Miyanishi, Harima-cho, Kako-gun, Hyogo 675-01, Japan
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Publication Date:
31 December 2000 (online)

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Treatment of 2,6-di-tert-butyl-4-methylphenyl 2-methoxybenzoate (5) with 4-methylphenylmagnesium bromide (6) in diethyl ether-benzene affords the 4’-methylbiphenyl-2-carboxylate (7) in excellent yield via an ester-assisted nucleophilic aromatic substitution (SNAr) reaction. Carboxylate 7 is in turn readily and quantitatively saponified to 4’-methylbiphenyl-2-carboxylic acid (2a) via transesterification by treatment with sodium methoxide in toluene-1-methyl-2-pyrrolidone followed by aqueous hydrolysis.

4’-Methyl-1,1’-biphenyl-2-carboxylic acid is easily prepared via the ester-assisted SNAr reaction