2-Methoxy-7-(4-methoxyphenyl)naphthalene → 7-(4-Hydroxyphenyl)-2-naphthol

HRID 895165Notes

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]=1

Participants

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 1 N 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)−.

Workup

temperaturecooled to room temperature
filtrationThe resulting suspension was filtered
dissolutiondissolved ethyl acetate (500 mL)
washThe combined organic layers were washed with water (200 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
customthe solvent removed under vacuum
customthe product purified by silica chromatography (40% ethyl acetate-hexanes

Sources & evidence

ORD record: ord-69e6ede2098e4c3a8c133c4ec4548fb9
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

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