Benzoic acid, 3-formyl-4-hydroxy-, methyl ester → Methyl 4-hydroxy-3-(hydroxymethyl)benzoate

Participants

Reaction Steps

A solution of methyl 3-formyl-4-hydroxybenzoate (19.80 g; 109.90 mmol; 1 eq.) in MeOH (396 mL) was added at 0° C. NaBH4 (6.24 g; 164.85 mmol; 1.50 eq.) in several portions (portions over 20 min). The reaction mixture was stirred at RT for 2 hours. The reaction mixture was concentrated and the residue was suspended in EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NH4Cl (2×200 mL), water (200 mL), then brine (200 mL). The aqueous layer contained a lot of the desired compound so it was saturated with NaCl and extracted with EtOAc (4×600 mL). Organics were combined, dried over MgSO4 and concentrated affording the title compound as a beige solid (10.52 g, 52%). LC/MS (Method B): 181.1 (M−H)−.

Provenance & Evidence