Water → 4,4'-Dimethylstilbene

HRID 735301Notes

Reaction equation

HRID 735301 reaction equation
[Br-].[CH3:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1.O>C1(C)C=CC=CC=1>[CH3:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[CH:7][C:6]2[CH:5]=[CH:4][C:3]([CH3:2])=[CH:28][CH:27]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 24758Sodium hydrideHCID 11797662Phosphonium, ((4-methylphenyl)methyl)triphenyl-, bromide (1:1)

Product 1

HCID 1376214,4'-DimethylstilbeneYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.4 g(5.37 mmol) of (4-methylbenzyl)triphenylphosphonium bromide and 0.98 g(60%, 24.4 mmol) of NaH were refluxed in toluene for 6 hours. After cooled down, 0.586 g(4.88 mmol) of 4-methylbenzaldehyde was introduced gradually to the solution to be refluxed again for 6 hours. The resulted product was treated with water to be extracted with ethyl acetate. The solvent was distilled off and the residue was recrystallized in ethanol. Yield; 71%.

Workup

  1. temperatureAfter cooled down
  2. temperatureto be refluxed again for 6 hours
  3. extractionto be extracted with ethyl acetate
  4. distillationThe solvent was distilled off
  5. customthe residue was recrystallized in ethanol

Sources & evidence

ORD record
ord-fa0b63b791f04268a0b40ec85769b29e
Source dataset
uspto-grants-2009_09
Patent number
US07592475B2

Reaction notes

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