Dimethyl Sulfate → 3,5-Dimethoxytoluene

HRID 1857131Notes

Reaction equation

HRID 1857131 reaction equation
[C:1]1([OH:9])[CH:8]=[C:6]([CH3:7])[CH:5]=[C:3](O)[CH:2]=1.S([O:15][CH3:16])(OC)(=O)=O.[C:17](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:17][O:9][C:1]1[CH:8]=[C:6]([CH3:7])[CH:5]=[C:3]([O:15][CH3:16])[CH:2]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10436OrcinolHCID 11430Potassium Carbonate

Product 1

HCID 778443,5-DimethoxytolueneYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Commercially available orcinol (5.77 g) was dissolved in acetonitrile (200 ml), dimethyl sulfate (8.47 ml) and potassium carbonate (12.3 g) were added, and the admixture was refluxed for 2.5 hours. The reaction mixture was poured into ice water and partitioned with chloroform, and the chloroform layer was dried with anhydrous magnesium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1) to obtain 5.04 g of the title compound (yield: 82%).

Workup

  1. temperaturethe admixture was refluxed for 2.5 hours
  2. custompartitioned with chloroform
  3. dry with materialthe chloroform layer was dried with anhydrous magnesium sulfate
  4. customThe solvent was removed by reduced-pressure distillation
  5. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1)

Sources & evidence

ORD record
ord-b72c9535f72646da81b688cef8ab241b
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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