2-Tert-Butylphenol → 1-(1,1-Dimethylethyl)-2-(methoxymethoxy)benzene

HRID 1296017Notes

Reaction equation

HRID 1296017 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5]Cl.[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])([CH3:10])([CH3:9])[CH3:8]>CN(C)C=O>[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:3][O:4][CH3:5])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 69232-Tert-ButylphenolHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 107742011-(1,1-Dimethylethyl)-2-(methoxymethoxy)benzeneYield 111.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (214 g, 4.90 mol) and chloromethyl methyl ether (394 g, 4.90) were gradually added to a solution of 2-tert-butylphenol (700 g, 4.67 mol) in dimethylformamide (3000 ml) while cooling on ice and the mixture was stirred at 0° C. for 2 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate, and then the organic layer was washed with water and brine in that order and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1013 g) as a light yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water and brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-129a919f9dbc416c91bb4bc243c5eb66
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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