1-Benzyloxy-4-diphenyl(tert-butyl)silyloxybenzene → 4-{[tert-Butyl(diphenyl)silyl]oxy}phenol

HRID 1634725Notes

Reaction equation

HRID 1634725 reaction equation
[C:1]([Si:5]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]CC2C=CC=CC=2)=[CH:21][CH:20]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C.C1CCCCC=1>[C:1]([Si:5]([O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 5326061-Benzyloxy-4-diphenyl(tert-butyl)silyloxybenzene

Product 1

HCID 138044024-{[tert-Butyl(diphenyl)silyl]oxy}phenolYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18676862Cyclohexene ethanolSolvent

Procedure

A mixture of t-butyl-[4-benzyloxyphenoxy]-diphenylsilane (170 g, 388 mmol) and 10 g of 10% palladium on carbon in ethanol-cyclohexene (2:1, v/v) was heated at reflux for 48 hours. The catalyst was filtered and the solvent was removed in vacuo to provide 134 g of product as an oil.

Workup

  1. temperaturev/v) was heated
  2. temperatureat reflux for 48 hours
  3. filtrationThe catalyst was filtered
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-799c079e360c4c3d821d82f827dd1198
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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