Potassium Bromide → 5-[(1E)-2-(3,4-dihydroxyphenyl)vinyl]-benzene1,2,3-triol

HRID 1795491Notes

Reaction equation

HRID 1795491 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]2[CH:18]=[C:17]([O:19]C)[C:16]([O:21]C)=[C:15]([O:23]C)[CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.Cl.N1C=CC=CC=1.[K+].[Br-]>>[OH:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]([OH:23])[C:16]([OH:21])=[C:17]([OH:19])[CH:18]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 3571821-(3,4-Dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethyleneHCID 10176127Pyridinium chloride

Product 1

HCID 117773655-[(1E)-2-(3,4-dihydroxyphenyl)vinyl]-benzene1,2,3-triol

Procedure

Demethylation: The 1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethylene (1.3 g) on demethylation with pyridine hydrochloride (7 g) under the conditions noted in example 1 gave 1, pp. 222–224° C.; IR (KBr) νmax 3450, 3338, 1608, 1535, 1449, 1320, 1177, 1119, 1035, 956, 848, 797 cm−1; 1H NMR (CH3OD, 400 MHz) δ 6.76 (1H, s), 6.61 (1H, d, J=8.0 Hz), 6.55 (1H, d, J=16.0 Hz), 6.54 (1H, d, J=8.0 Hz), 6.50 (1H, d, J=16.0 Hz), 6.33 (2H, s).

Workup

  1. customgave 1
  2. custom222–224° C.

Sources & evidence

ORD record
ord-ed9c831a7f054685b5c3c4bbcd7e1fea
Source dataset
uspto-grants-2006_04
Patent number
US07026518B2

Reaction notes

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