1-Chloro-2-methoxy-6-(4-methoxyphenyl)naphthalene → 1-Chloro-6-(4-hydroxyphenyl)-2-naphthol

HRID 1830629Notes

Reaction equation

HRID 1830629 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:20]C.Cl.[NH+]1C=CC=CC=1>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:20]

Participants

3

Reactant 2

HCID 111623351-Chloro-2-methoxy-6-(4-methoxyphenyl)naphthaleneHCID 21584435Pyridinium hydrochloride

Product 1

HCID 61026901-Chloro-6-(4-hydroxyphenyl)-2-naphthol

Procedure

The title compound was prepared by reacting 1-chloro-2-methoxy-6-(4-methoxyphenyl)naphthalene (0.32 g, 1.07 mmol) with pyridinium HCl (7g) at 190° C. according to method B to yield 0.12 g (41%) of an off white solid: mp 222–224° C. (dec.); 1H NMR (DMSO-d6): δ 6.88 (2H, d, J=8.46 Hz), 7.29 (1H, d, J=8.88 Hz), 7.63 (2H d, J=8.50 Hz), 7.81–7.88 (2H, m), 8.02–8.08 (2H, m), 9.59 (1H, s), 10.43(1H, s); MS (ESI) m/z 269/271(M−H)−.

Workup

  1. customat 190° C.
  2. customto yield 0.12 g (41%) of an off white solid

Sources & evidence

ORD record
ord-31ccfa8798494972b9bda98bf3dcf0e2
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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