2-Benzyloxystilbene → 2-(2-Phenylethyl)phenol

HRID 743407Notes

Reaction equation

HRID 743407 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:17]1([CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 544184572-BenzyloxystilbeneHCID 178418361HCID 178418361, compound

Product 1

HCID 27490412-(2-Phenylethyl)phenolYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The whole of this 2-benzyloxystilbene was dissolved in 300 ml of ethanol, and the resulting solution was stirred at 60° C. for 3.5 hours in an atmosphere of hydrogen at atmospheric pressure and in the presence of 1.00 g of 5% w/w palladium-on-charcoal. The catalyst was removed by filtration, and the filtrate was concentrated by distillation 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 6.41 g (yield 89%) of the title compound as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-75388ea5bbef4b939c8d1ddf200cf6cb
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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