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

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)−.

1. customin several portions (portions over 20 min)
2. concentrationThe reaction mixture was concentrated
3. washThe organic layer was washed with a saturated aqueous solution of NH4Cl (2×200 mL), water (200 mL)
4. extractionextracted with EtOAc (4×600 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated

ORD record

ord-631885649c444d74a204c192e0d77d70

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202865B2