3,5-Dimethoxybenzaldehyde → 1,3-Dimethoxy-5-(2-phenylethenyl)benzene

HRID 2414704Notes

Reaction equation

HRID 2414704 reaction equation
C[O-].[Na+].P(=O)([O-])O[C:6]([CH2:15][CH3:16])(CC)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:19][O:20][C:21]1[CH:22]=C([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1)C=O>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:16]([CH:15]=[CH:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1

Participants

5

Reactant 3

HCID 817473,5-DimethoxybenzaldehydeHCID 10942334Sodium MethoxideHCID 178447633HCID 178447633, compound

Product 1

HCID 2387781,3-Dimethoxy-5-(2-phenylethenyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.5 g (0.3 mol) of sodium methanolate are added at 0° C. to a solution of 60 g (0.29 mol) of crude diethylbenzyl phosphonate in 415 ml of anhydrous DMF. Then, at 0° C., a total of 50.0 g (0.3 mol) of 3,5-dimethoxybenzaldehyde is added in portions. After stirring for 1 hour at room temperature and heating for 1 hour under reflux, the product is precipitated by the addition of 660 ml of water/methanol (mixture ratio 2:1). Recrystallisation from water/methanol (2:1) yields 3,5-dimethoxystilbene in the form of colourless crystals.

Workup

  1. temperatureheating for 1 hour
  2. temperatureunder reflux
  3. customthe product is precipitated by the addition of 660 ml of water/methanol (mixture ratio 2:1)
  4. customRecrystallisation from water/methanol (2:1)

Sources & evidence

ORD record
ord-53ca7e5bce8d4138adea6820692a862a
Source dataset
uspto-grants-2004_11
Patent number
US06814960B1

Reaction notes

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