2-Methoxy-6-(3-methoxyphenyl)naphthalene → 6-(3-Hydroxyphenyl)-2-naphthol

HRID 895176Notes

Reaction equation

HRID 895176 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[CH:9]=2)[CH:4]=1.Cl.[NH+]1C=CC=CC=1>>[OH:19][C:15]1[CH:14]=[C:13]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]3)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 114028342-Methoxy-6-(3-methoxyphenyl)naphthaleneHCID 21584435Pyridinium hydrochloride

Product 1

HCID 101927306-(3-Hydroxyphenyl)-2-naphthol

Procedure

The title compound was prepared by reacting 2-methoxy-6-(3-methoxyphenyl)naphthalene (0.51 g, 1.90 mmol) with pyridinium HCl (6 g) at 190° C. according to method B to yield 0.21 g (47%) of an off white solid: mp 192-194° C.; 1H NMR (DMSO-d6): δ 6.75-6.78 (1H, m), 7.10-7.14 (3H, m), 7.16-7.18 (1H, m), 7.65 (1H, dd, J=1.79 Hz, J=8.57 Hz), 7.75 (1H, d, J=8.77 Hz), 7.84 (1H, d, J=8.77 Hz), 8.01 (1H, d, J=1.59 Hz), 9.51 (1H, s), 9.78, (1H, s); MS (ESI) m/z 235 (M−H)−. Anal. for C16H12O2:

Workup

  1. customat 190° C.
  2. customto yield 0.21 g (47%) of an off white solid

Sources & evidence

ORD record
ord-1784977645a6472e83c6037b8e14757d
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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