1-(2-Benzyloxyphenyl)-4-(3-chlorophenyl)butadiene → 1-(2-Benzyloxyphenyl)-4-(3-chlorophenyl)butane

HRID 743400Notes

Reaction equation

HRID 743400 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>O1CCCC1.C(O)C.[Pd]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 545226781-(2-Benzyloxyphenyl)-4-(3-chlorophenyl)butadieneHCID 178418361HCID 178418361, compound

Product 1

HCID 194240571-(2-Benzyloxyphenyl)-4-(3-chlorophenyl)butaneYield 86.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.50 g of this 1-(2-benzyloxyphenyl)-4-(3-chlorophenyl)butadiene were dissolved in 125 ml of a 4:1 by volume mixture of tetrahydrofuran and ethanol. The resulting solution was stirred for 4 hours in an atmosphere of hydrogen at atmospheric pressure and in the presence of 100 mg of 5% w/w palladium-on-charcoal, whilst ice-cooling. At the end of this time, the catalyst was removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was then purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.06 g (yield 86%) of 1-(2-benzyloxyphenyl)-4-(3-chlorophenyl)butane as a colorless oil.

Workup

  1. temperaturecooling
  2. customAt the end of this time, the catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. customThe resulting residue was then purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-43e59bb6024a47fba52afdf804f1fec6
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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