Convenient Synthesis of Biphenyl-2-carboxylic Acids via the Nucleophilic Aromatic Substitution Reaction of 2-Methoxybenzoates by Aryl Grignard Reagents.

T Hattori, T Suzuki, N Hayashizaka, N Koike…

Index: Hattori, Tetsutaro; Suzuki, Takatsugu; Hayashizaka, Noriyuki; Koike, Nobuyuki; Miyano, Sotaro Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 10 p. 3034 - 3040

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Citation Number: 34

Abstract

Nucleophilic aromatic substitution (SN Ar) of 2-methoxybenzoic esters derived from 2, 6- dialkylphenols by aryl Grignard reagents affords 1, 1′-biphenyl-2-carboxylates in excellent yields by proper choice of the bulk of the 2, 6-dialkyl-substituents. The phenoxyl protecting groups can be easily removed from the resulting biphenyl-2-carboxylates to the free acids by treatment with potassium hydroxide in aqueous ethanol (2, 4, 6-trimethylphenyl and 2, 6- ...

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