2-Methoxy-7-(4-methoxyphenyl)naphthalene → 7-(4-Hydroxyphenyl)-2-naphthol
Reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[CH:4]=1.Cl.[NH+]1C=CC=CC=1>Cl>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:7]2[CH:6]=[C:5]3[C:10]([CH:11]=[CH:12][C:3]([OH:2])=[CH:4]3)=[CH:9][CH:8]=2)=[CH:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 190 °C
Procedure
2-Methoxy-7-(4-methoxy-phenyl)naphthalene (1.02 g, 3.86 mmol) was added to of pyridinium HCl (10 g) at 190° C. The solution was stirred for 3 hr at 190° C. and cooled to room temperature and stirred with 200 mL of 1N HCl. The resulting suspension was filtered and dissolved ethyl acetate (500 mL). The combined organic layers were washed with water (200 mL), dried over magnesium sulfate, filtered, the solvent removed under vacuum, and the product purified by silica chromatography (40% ethyl acetate-hexanes to yield 0.36 g (39%) of a white solid: mp 210° C.; 1H NMR (DMSO-d6): δ 6.89 (2H, d, J=8.58 Hz), 7.05 (1H, dd, J=2.42 Hz, J=8.77 Hz), 7.17 (1H, d, J=2.24 Hz), 7.52 (1H, dd, J=1.68 Hz, J=8.40 Hz), 7.61. (2H, d, J=8.58 Hz), 7.74 (1H, d, J=8.58 Hz), 7.79 (1H, d, J=8.58 Hz), 7.86 (1H, d, J=1.12 Hz), 9.60 (1H, bs), 9.72 (1H, bs); MS (ESI) m/z 235 (M−H)−.