Isovanillin → (E)-3-Hydroxy-4,4'-dimethoxystilbene

HRID 1839529Notes

Reaction equation

HRID 1839529 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][C:33]=1[OH:40].[OH-].[Na+]>C(Cl)Cl.O>[OH:40][C:33]1[CH:34]=[C:35](/[CH:36]=[CH:8]/[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:29][CH:28]=2)[CH:38]=[CH:39][C:32]=1[O:31][CH3:30]

Participants

6

Reactant 3

HCID 12127IsovanillinHCID 14798Sodium HydroxideHCID 2773651(4-Methoxybenzyl)triphenylphosphonium chloride

Product 1

HCID 23450398(E)-3-Hydroxy-4,4'-dimethoxystilbeneYield 3.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-methoxybenzyltriphenylphosphonium chloride (5.51 g, 13mmol) and 4-methoxy-3-hydroxybenzaldehyde (2 g, 13 mmol) in CH2Cl2 was added a cooled aqueous solution of NaOH(62.5 eq) in H2O. The mixture was stirred at room temperature for 48 h. The aqueous layer was then acidified to pH 5 and the precipitated solid was filtered and dried. Purification by silica gel chromatography using hexane/ethyl acetate (1:1) gave the title E-trans product as a colourless solid 0.11 g (3%): 1H NMR (DMSO) δ 9.3 (1H, bs). 7.6 (2H, d), 7.2 (7H, m), 3.5 (6H, s): Mass Spectrum (FAB) 257 (M+1).

Workup

  1. filtrationthe precipitated solid was filtered
  2. customdried
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-be214ab8df2c4b01a0b08d57f78efb70
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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