Dimethyl Sulfate → 2-Isopropylanisole

HRID 1609712Notes

Reaction equation

HRID 1609712 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].S(OC)(O[CH3:15])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 69432-IsopropylphenolHCID 11430Potassium Carbonate

Product 1

HCID 2706232-Isopropylanisole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Isopropylphenol (300 g), 262 ml of dimethyl sulfate, and 1500 g of potassium carbonate in 1 liter of acetone are stirred mechanically and refluxed for61/2 hours. The mixture is filtered and the filter cake washed with acetone. The combined filtrate is stripped, the residue is redissolved in ether, then extracted with 2N sodium hydroxide (twice) and brine (once). The ether is dried, filtered, and stripped to leave an oil which is distilled under high vacuum to afford 2-isopropylanisole, b.p. 39°.

Workup

  1. temperaturerefluxed for61/2 hours
  2. filtrationThe mixture is filtered
  3. washthe filter cake washed with acetone
  4. dissolutionthe residue is redissolved in ether
  5. extractionextracted with 2N sodium hydroxide (twice) and brine (once)
  6. dry with materialThe ether is dried
  7. filtrationfiltered
  8. customto leave an oil which
  9. distillationis distilled under high vacuum

Sources & evidence

ORD record
ord-e6bc0d2b1dc24ef498b7b613a254b2c1
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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