Hydroquinone → 4-(tert-Butyldimethylsiloxy)phenol

HRID 2395923Notes

Reaction equation

HRID 2395923 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1.C(OCC)(=O)C.CCCCCC>CN(C=O)C.O>[Si:9]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 5973884-(tert-Butyldimethylsiloxy)phenolYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of hydroquinone (1.0 g, 0.9 mmol) and tert-butyldimethylsilylchloride (1.4 g, 0.9 mmol) in 5 mL of dry DMF was gradually added imidazole(1.2 g, 1.8 mmol) and the solution was stirred for 1 hour. TLC analysis (silica gel, 20% ethyl acetate/hexane) showed completion of reaction. The solution was poured into 25 mL of water and extracted with 3×25 mL of ether. The combined ether solutions were dried over anhydrous MgSO4. Evaporation of solvent gave an oil which was chromatographed on silica using 20% ethyl acetate/hexane to give the product as a white solid in 70% yield: 1H NMR (CDCl3) δ0.145 (s, 6H), 0.956 (s, 9H), 4.47 (bs, 1H), 6.68 (s, 4H); 13C NMR (CDCl3) δ-4.48, 18.21, 25.74, 115.93, 120.55, 120.81, 149.78.

Workup

  1. customcompletion of reaction
  2. extractionextracted with 3×25 mL of ether
  3. dry with materialThe combined ether solutions were dried over anhydrous MgSO4
  4. customEvaporation of solvent
  5. customgave an oil which
  6. customwas chromatographed on silica using 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7ae118b757ab4bc1895c6c85ecad679b
Source dataset
uspto-grants-1996_02
Patent number
US05491072

Reaction notes

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