4,4'-Dimethoxybenzophenone → 1,1-bis(4-methoxyphenyl)ethylene

HRID 2296842Notes

Reaction equation

HRID 2296842 reaction equation
C[Mg]Br.[CH2:4](OCC)C.[CH3:9][O:10][C:11]1[CH:26]=[CH:25][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=O)=[CH:13][CH:12]=1>C(OCC)C>[CH3:9][O:10][C:11]1[CH:26]=[CH:25][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH2:4])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 70324,4'-DimethoxybenzophenoneHCID 178467822HCID 178467822, compound

Product 1

HCID 3167241,1-bis(4-methoxyphenyl)ethylene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An equivalent of methyl magnesium bromide/diethyl ether solution is reacted with 4,4′-dimethoxybenzophenone (24.2 g, 0.1 mol) dissolved in anhydrous diethyl ether over a 60 minute period at ambient temperature. The reaction mixture is poured onto ice and extracted with ether. The ether is removed by distillation and replaced with ethyl acetate (100 mL). The ethyl acetate solution is refluxed for one hour over anhydrous magnesium sulfate. Methylene chloride (300 mL) is added and the magnesium sulfate removed by filtration. The solvent is distilled leaving 16.9 g of the title compound as a white solid melting at 137° C. whose structure is consistent with 1Hnmr and mass spectrometry.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted with ether
  3. customThe ether is removed by distillation
  4. temperatureThe ethyl acetate solution is refluxed for one hour over anhydrous magnesium sulfate
  5. additionMethylene chloride (300 mL) is added
  6. customthe magnesium sulfate removed by filtration
  7. distillationThe solvent is distilled

Sources & evidence

ORD record
ord-bd24f0feed454cb99cb512c997eadf98
Source dataset
uspto-grants-2002_12
Patent number
US06489383B1

Reaction notes

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