4-(4-Ethoxyphenoxy)-2-isopropylphenyl benzyl ether → 2-Isopropyl-4-(4-ethoxyphenoxy)phenol

HRID 260789Notes

Reaction equation

HRID 260789 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH:25]([CH3:27])[CH3:26])C1C=CC=CC=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[CH:25]([C:10]1[CH:11]=[C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)[CH:13]=[CH:14][C:9]=1[OH:8])([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 214662534-(4-Ethoxyphenoxy)-2-isopropylphenyl benzyl etherHCID 178418361HCID 178418361, compound2×

Product 1

HCID 214662942-Isopropyl-4-(4-ethoxyphenoxy)phenolYield 93.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Then, 4.4 g of 4-(4-ethoxyphenoxy)-2-isopropylphenyl benzyl ether and 100 ml of ethyl acetate were charged into a reaction vessel, and air in the vessel was replaced with nitrogen. Then, 0.50 g of 5% palladium-carbon was added, and nitrogen in the vessel was replaced with hydrogen, followed by vigorous stirring at room temperature for 24 hours. After hydrogen in the vessel was replaced with nitrogen, the reaction vessel was filtered with Celite, and the flitrate was concentrated. The residue was subjected to silica gel chromatography to give 3.1 g of 2-isopropyl-4-(4-ethoxyphenoxy)phenol (yield, 93%).

Workup

  1. filtrationthe reaction vessel was filtered with Celite
  2. concentrationthe flitrate was concentrated

Sources & evidence

ORD record
ord-41f7ceb7a19542a4aa32517cc69f958b
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Reaction notes

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