Ethyl Acetate → 4-(2-Phenethyloxyethoxy)phenol

HRID 1905975Notes

Reaction equation

HRID 1905975 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(OCC)(=O)C>C(O)C.[Pd]>[CH2:19]([O:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 202137271-Benzyloxy-4-(2-phenethyloxyethoxy)benzene

Product 1

HCID 202137204-(2-Phenethyloxyethoxy)phenolYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 1-benzyloxy-4-(2-phenethyloxyethoxy)benzene obtained according to the preceding paragraph was dissolved in 200 ml of ethanol and 200 ml of ethyl acetate and hydrogenated overnight at atmospheric pressure and room temperature in the presence of 0.4 g of 10% palladium/carbon. The catalyst was removed by filtration and the filtrate was evaporated to give 10.8 g (91%) of 4-(2-phenethyloxyethoxy)phenol in the form of an oil which was homogeneous according to chromatography.

Workup

  1. customat atmospheric pressure and room temperature
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0e006ecf2e0540c9b023e26ed794f5cc
Source dataset
uspto-grants-1987_03
Patent number
US04649160

Reaction notes

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