Sodium Hydroxide → 5-Chloro-4-iodo-2-methoxybenzoic acid

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Reaction Steps

A mixture od 5-chloro-4-iodo-2-methoxy benzoic acid methyl ester of Step B (3.00 g, 9.19 mmol) and sodium hydroxide (1.10 g, 27.6 mmol) in methanol (92 mL) was refluxed for 12 hours. The reaction was cooled to room temperature and the solvent evaporated. The residue was dissolved in 1 N sodium hydroxide (75 mL), the solution washed with diethyl ether and the organic washings discarded. The aqueous phase was acidified with 2 N hydrochloric acid and extracted with diethyl ether. The combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated to afford the title carboxylic acid (2.64 g) as orange crystals, m.p. 150-151° C.

Provenance & Evidence