Pyridinium hydrochloride → 7-Phenylnaphthalen-2-ol

HRID 895167Notes

Reaction equation

HRID 895167 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]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[CH:4]=1.Cl.[NH+]1C=CC=CC=1>>[C:13]1([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]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 220481542-Methoxy-7-phenylnaphthalene

Product 1

HCID 114586747-Phenylnaphthalen-2-ol

Procedure

The title compound was prepared by reacting 2-methoxy-7-phenylnaphthalene (0.53 g, 2.26 mmol) with pyridinium HCl (10 g) at 190° C. according to method B to yield 0.36 g (72%) of a white solid: mp 142-143° C.; 1H NMR (DMSO-d6): δ 7.10 (1H, dd, J=2.75 Hz, J=8.70 Hz), 7.23 (1H, d, J=2.29 Hz), 7.37-7.40 (1H, m), 7.48-7.51 (2H, m), 7.58 (1H, dd, J=1.83 Hz, 8.70 Hz), 7.78-7.90 (3H, m), 7.86 (1H, d, J=8.24 Hz), 7.99 (1H, d, J=0.92 Hz) 9.81 (1H, s); MS (ESI) m/z 219 (M−H)−.

Workup

  1. customat 190° C.

Sources & evidence

ORD record
ord-e1b140d6d58644e2bc68b75cc35bcb99
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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