3588-75-8

569-42-6

74-88-4

3588-75-8

The synthetic procedure was modified based on literature reports. 1,8-Dihydroxynaphthalene (200 mg, 1.25 mmol) was dissolved in 10 mL of acetone and K2CO3 (207 mg, 1.50 mmol) and CH3I (117 μL, 1.88 mmol) were added sequentially. The resulting inhomogeneous mixture was stirred for 24 h at room temperature. After completion of the reaction, the reaction was quenched with H2O (5 mL) and treated with saturated NH4Cl solution (5 mL). The aqueous phase was extracted with EtOAc (2 × 10 mL). The combined organic phases were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. Purification by fast column chromatography (EtOAc:hexane = 1:19) afforded 1-methoxy-8-naphthol (210 mg, 96%) as a white solid. All spectral data were in agreement with the values reported in the literature.Rf = 0.51 (EtOAc:hexane = 1:9); 1H NMR (400 MHz, CDCl3): δ 9.32 (1H, s), 7.43 (1H, dd, J = 8.3, 0.4 Hz), 7.36 (1H, t, J = 8.0 Hz), 7.33-7.29 (2H, m), 6.88 (1H, dd, J = 7.4, 1.2 Hz), 6.78 (1H, d, J = 7.7 Hz), 4.06 (3H, s); 13C NMR (100 MHz, CDCl3): δ 156.3, 154.6, 136.9, 127.8, 125.7, 122.0, 119.0, 115.2, 110.5, 104.0, 56.2; FTIR (ATR, solids): 3352, 3051, 2951, 2844, 1629, 1609, 1580, 1513, 1451, 1397, 1307, 1227 cm-1; HRMS (APCI+) calculated C11H11O2 [M+H]+: 175.0754, measured. 175.0759.