Hydroquinone → 4-(tert-Butyldimethylsiloxy)phenol

HRID 504996Notes

Reaction equation

HRID 504996 reaction equation
N1C=CN=C1.[C:6]1([CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)[OH:7].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C)C=O.O>[Si:14]([O:7][C:6]1[CH:13]=[CH:12][C:10]([OH:11])=[CH:9][CH:8]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 5973884-(tert-Butyldimethylsiloxy)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.9 parts of imidazole, 1.99 parts of hydroquinone and 3 parts of tert-butyldimethylsilyl chloride in 10 mL of dimethylformamide was stirred at room temperature for 1 hr 45 min. The reaction was monitored by TLC showed formation of product. The reaction mixture was diluted with 50 mL of deionized water and product was extracted with 2×50 mL of ether. The combined organic layer was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel with 5% ethyl acetate-hexanes to yield 2.24 parts 4-(tert-butyldimethylsilyloxy)phenol. NMR was used to confirm the following structure.

Workup

  1. extractionwas extracted with 2×50 mL of ether
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography on silica gel with 5% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-5ebfe4165b114690a02b87895ef24801
Source dataset
uspto-grants-2010_08
Patent number
US07781229B2

Reaction notes

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