Methyl 3-aminophenylacetate → 3-(Methylthio)phenylacetic acid

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Prepared in an essentially similar fashion from methyl 3-aminophenyl-acetate (111 g, 0.67 mole) and potassium methanethiolate (2.68 mole) to give 3-methylthiophenylacetic acid (21.0 g). Mp=76-77° C., 1H NMR (DMSO-d6, 200 MHz) δ: 2.44 (s, 3H, SCH3), 3.53 (s, 2H, ArCH2), 7.02-7.28 (m, 4H, Ar), 12.30 (br s, 1H, CO2H). Mass spectrum (CI—CH4): 183 (M+1, 100%). (Lit. ref.: Plant Physiol 42(11) 2596-1600 (1967).

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