2-Methoxy-7-(3-methoxyphenyl)naphthalene → 7-(3-Hydroxyphenyl)-2-naphthol

HRID 895166Notes

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][CH:16]=[C:15]([O:19]C)[CH:14]=3)=[CH:8][CH:9]=2)[CH:4]=1.Cl.[NH+]1C=CC=CC=1>>[OH:19][C:15]1[CH:14]=[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:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 114484492-Methoxy-7-(3-methoxyphenyl)naphthalene

HCID 21584435Pyridinium hydrochloride

Product 1

HCID 101714107-(3-Hydroxyphenyl)-2-naphthol

Procedure

The title compound was prepared by reacting 2-methoxy-7-(3-methoxyphenyl)naphthalene (0.52 g, 1.97 mmol) with pyridinium HCl (8 g) at 190° C. according to Method B to yield 0.13 g (28%) of a white solid: mp 163-165° C.; 1H NMR (DMSO-d6): δ 6.78-6.80 (1H, m), 7.08 (1H, dd, J=2.56 Hz, J=8.54 Hz), 7.13-7.14 (1H, m), 7.17-7.20 (2H, m), 7.27-7.30 (1H, m), 7.51 (1H, dd, J=2.14 Hz, J=8.54 Hz), 7.70 (1H, d, J=8.97 Hz), 7.83 (1H, d, J=8.54 Hz), 7.90 (1H, d, J=1.28 Hz), 9.55 (1H, s), 9.78 (1H, s); MS (ESI) m/z235 (M−H)−.

Workup

customat 190° C.

Sources & evidence

ORD record: ord-fd833d90986b4bc3a82f59561de120a9
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

Loading…