1-(2-Benzyloxyphenyl)-4-phenylbutadiene → 2-(4-Phenylbutyl)phenol

HRID 743383Notes

Reaction equation

HRID 743383 reaction equation
C([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]=[CH:21][CH:20]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[C:19]1([CH2:18][CH2:17][CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 545219991-(2-Benzyloxyphenyl)-4-phenylbutadieneHCID 178418361HCID 178418361, compound

Product 1

HCID 125964892-(4-Phenylbutyl)phenolYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The whole of this 1-(2-benzyloxyphenyl)-4-phenylbutadiene was mixed with 300 ml of ethanol, and the mixture was stirred at 60° C. for 5 hours in an atmosphere of hydrogen and in the presence of 1 g of 5% w/w palladium-on-charcoal. 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 purified by column chromatography through silica gel, using a 8:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 8.34 g (yield 94.4%) of the title compound as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-0f83c7ee5682429eaf27911eb0e51576
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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