Potassium Carbonate → 2,6-Dimethyl-4-[(trimethylsilyl)methoxy]phenol

HRID 1737190Notes

Reaction equation

HRID 1737190 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[OH:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O>[CH3:1][C:2]1[CH:8]=[C:7]([O:9][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:6]=[C:5]([CH3:10])[C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 695602,6-DimethylhydroquinoneHCID 75361Silane, (chloromethyl)trimethyl-

Product 1

HCID 158723362,6-Dimethyl-4-[(trimethylsilyl)methoxy]phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix 2,6-dimethylhydroquinone (1.4 g, 10 mmol), potassium carbonate (1.4 g, 10 mmol), chloromethyltrimethylsilane (1.9 g, 10 mmol) and dimethylformamide (50 mL). Stir at room temperature under inert atmosphere until the reaction is complete. Dilute the mixture with ice-water and extract with ethyl ether. Wash the ethereal layer with water, then brine and filter through fluorosil-Na2SO4. Evaporate to give the title compound and purify by silica gel chromatography.

Workup

  1. extractionextract with ethyl ether
  2. washWash the ethereal layer with water
  3. filtrationbrine and filter through fluorosil-Na2SO4
  4. customEvaporate

Sources & evidence

ORD record
ord-820b353020b94ccd92ec2ec87be0098d
Source dataset
uspto-grants-1999_10
Patent number
US05962435

Reaction notes

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