Dimethyl Sulfate → 2-Isopropylanisole

HRID 865996Notes

Reaction equation

HRID 865996 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 for 61/2 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 for 61/2 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-60213fb03ede4ec9b43d4f5b725d23d9
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Reaction notes

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