Water → Methyl 2-chloro-4-(hydroxymethyl)benzoate

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Reaction Steps

Borane-methyl sulfide complex (10 M; 10 Ml, 100 mmol) was added to a solution of 2-chloro-1,4-benzenedicarboxylic acid, 1-methyl ester (Example 1; 11.98 g, 55.8 mmol) in tetrahydrofuran (100Ml). The solution was heated at reflux for 2 h and then allowed to stand at room temperature overnight. It was poured into water and ethyl acetate (200 Ml each). The layers were separated and the aqueous layer was extracted with ethyl acetate (100 Ml). The combined organic layers were washed with brine (200 Ml), dried (MgSO4), filtered, and evaporated to give 2-chloro-4-(hydroxymethyl)benzoic acid, methyl ester (11.09 g, 99%) as a colorless oil.

Provenance & Evidence