Practical synthesis of 4'-methylbiphenyl-2-carboxylic acid

T. Hattori, N. Hayashizaka, S. Miyano

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

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 (S(N)Ar) 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.

Original languageEnglish
Pages (from-to)41-43
Number of pages3
JournalSynthesis
Issue number1
DOIs
Publication statusPublished - 1995

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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