Synthesis p. 41 - 43 (1995)
Update date:2022-08-05
Topics:
Hattori
Hayashizaka
Miyano
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.
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Doi:10.1055/s-2005-872659
(2005)Doi:10.1055/s-2005-872660
(2005)Doi:10.1021/jo051360d
(2005)Doi:10.1246/cl.2007.316
(2007)Doi:10.1016/S0040-4039(00)81760-8
(1983)Doi:10.1016/S0040-4039(00)81690-1
(1983)
