Dimethyl Sulfate → 2-Isopropylanisole

HRID 2256478Notes

Reaction equation

HRID 2256478 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 61/2hours. 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 sodira 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 61/2hours
  2. filtrationThe mixture is filtered
  3. washthe filter cake washed with acetone
  4. dissolutionthe residue is redissolved in ether
  5. extractionextracted with 2N sodira 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-4f667ac0fd8b41cc8dcd5eeedb80a27e
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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