Acetic Acid → 4-Methylthio-3-nitrobenzoic acid

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Reaction Steps

A solution of methyl 4-methylthio-3-nitrobenzoate (11.7 g) and sodium hydroxide (4.1 g) in ethanol (234 ml) and water (117 ml) was heated at reflux for 2 hours and was then concentrated in vacuo to about 70 ml. Water (250 ml) was added and the mixture was warmed to give a solution which was acidified with acetic acid (30 ml). The mixture was stirred while cooling and the resulting solid collected and washed with water to yield 4-methylthio-3-nitrobenzoic acid (10.3 g), m.p. 245°-247° C. [Elemental analysis: C,45.2; H,3.22; N,6.48; S,14.1%; calculated: C,45.07; H,3.29; N,6.57; S,15.02%].

Provenance & Evidence