Lithium Hydroxide → 2-Chloro-4-methylbenzoic acid

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To methyl 2-chloro-4-methylbenzoate (1.00 g, 5.42 mmol) in THF (10 mL) MeOH (5 mL) and H2O (2.5 mL) is added 2N LiOH (8.12 mL, 16.2 mmol). The reaction mixture is heated at 50° C. for 2.5 hr, cooled to room temperature, then quenched with 5N HCl (3.24 mL). The mixture is concentrated to remove the TBF and MeOH. A white precipitate is formed and is filtered. After drying, 0.922 g (100%) of 2-chloro-4-methylbenzoic acid is isolated. ESIMS m/e 169 (M−−1; 35Cl) and 171 (M−−1; 37Cl).

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