Water → Methyl 3-Methoxy-2-naphthoate

A slurry of methyl 3-hydroxy-2-naphthoate (10.1 g, 50.1 mmol) and K2CO3 (7.96 g, 57.6 mmol) in DMF (200 mL) was stirred at room temp. for 15 min., then treated with iodomethane (3.43 mL, 55.1 mmol). The mixture was allowed to stir at room temp. overnight, then was treated with water (200 mL). The resulting mixture was extracted with EtOAc (2×200 mL). The combined organic layers were washed with a saturated NaCl solution (100 mL), dried (MgSO4), concentrated under reduced pressure (approximately 0.4 mmHg overnight) to give methyl 3-methoxy-2-naphthoate as an amber oil (10.30 g): 1H-NMR (DMSO-d6) δ2.70 (s, 3H), 2.85 (s, 3H), 7.38 (app t, J=8.09 Hz, 1H), 7.44 (s, 1H), 7.53 (app t, J=8.09 Hz, 1H), 7.84 (d, J=8.09 Hz, 1H), 7.90 (s, 1H), 8.21 (s, 1H). Step 2. 3-Methoxy-2-naphthoic acid

1. extractionThe resulting mixture was extracted with EtOAc (2×200 mL)
2. washThe combined organic layers were washed with a saturated NaCl solution (100 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated under reduced pressure (approximately 0.4 mmHg overnight)

ORD record

ord-1bead707131647c8b54677dc43d05266

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07235576B1