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

HRID 1830614Notes

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 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)−.

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-f601d44584ef495185ef7dc45327efb9
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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