Lithium hydroxide, monohydrate → 4-Cyano-2-methylbenzoic acid

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Reaction Steps

To a solution of 4-cyano-2-methylbenzoic acid methyl ester (Example 3.6) (61 g, 348 mmol) in a mixture of water (0.360 ml) and tetrahydrofuran (1.4 l) was added lithium hydroxide hydrate (31.4 g, 748.2 mmol). The reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated. The residue was acidified by addition of aqueous hydrochloric acid (1N) and extracted with a mixture of methanol and chloroform (5:95). The organic phase was dried over sodium sulfate and concentrated. The residue was crystallized in a mixture of ethyl acetate andcyclohexane to give 4-cyano-2-methylbenzoic acid (55.5 g, 99% yield).

Provenance & Evidence