Sodium borohydride → 4-(Hydroxymethyl)-2-methylbenzoic acid

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Reaction Conditions

Reaction Steps

To 4-formyl-2-methylbenzoic acid (75 mg, 0.46 mmol), in methanol (5 ml), was added sodium borohydride (26 mg, 0.69 mmol). The solution was stirred at 25° C. for 1 h. The reaction was quenched with saturated aqueous ammonium chloride and the pH adjusted to 2 with 2 N aqueous hydrochloric acid, then extracted with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude 4-(hydroxymethyl)-2-methylbenzoic acid (37 mg, 76%) was obtained and was used without further purification. 1H NMR (400 MHz, DMSO): 12.73-12.68 (s, 1H), 7.82-7.77 (d, 1H), 7.24-7.19 (m, 2H), 5.32-5.27 (m, 1H), 4.53-4.48 (d, 2H), 2.53-2.49 (s, 3H). MS (EI) for C9H10O3: 167 (MH+).

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