3,4,5-Trimethoxybenzaldehyde → (E)-3,4,5,4′-Tetramethoxystilbene

HRID 1839531Notes

Reaction equation

HRID 1839531 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:33]=[C:34]([CH:37]=[C:38]([O:42][CH3:43])[C:39]=1[O:40][CH3:41])[CH:35]=O.[OH-].[Na+]>C(Cl)Cl.O>[CH3:43][O:42][C:38]1[CH:37]=[C:34](/[CH:35]=[CH:8]/[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:29][CH:28]=2)[CH:33]=[C:32]([O:31][CH3:30])[C:39]=1[O:40][CH3:41]

Participants

6

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 14798Sodium HydroxideHCID 2773651(4-Methoxybenzyl)triphenylphosphonium chloride

Product 1

HCID 5388065(E)-3,4,5,4′-Tetramethoxystilbene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-methoxybenzyltriphenylphosphonium chloride (6.4 g, 15.3 mmol) and 3,4,5-trimethoxybenzaldehyde (3 g, 15.3 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 hours. The organic phase was separated and the aqueous phase was washed with CH2Cl2. The organic phase was concentrated and the residue was recrystallised from ethanol to yield the title E-trans isomer. 1H NMR (CDCl3) δ 8.7 (1H, d:), 8.2 (4H, m), 8.0 (2H, s), 5.2 (6H, s), 5.0 (6H, s). Mass Spectrum (FAB) 301 (M+1).

Workup

  1. customThe organic phase was separated
  2. washthe aqueous phase was washed with CH2Cl2
  3. concentrationThe organic phase was concentrated
  4. customthe residue was recrystallised from ethanol
  5. customto yield the title E-trans isomer

Sources & evidence

ORD record
ord-cad90b478050461a9caf87006ab1a89c
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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