Methyl iodide → 2,3,4,5-tetramethoxytoluene

HRID 1527656Notes

Reaction equation

HRID 1527656 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([O:11][CH3:12])[C:3]=1[O:13][CH3:14].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:14][O:13][C:3]1[C:4]([O:11][CH3:12])=[C:5]([O:10][CH3:15])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 249755962,3,6-Trimethoxy-4-methylphenol

Product 1

HCID 98777642,3,4,5-tetramethoxytolueneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

According to a modification of the procedure by Brimble et al.,36 11 (0.660 g, 3.33 mmol) and K2CO3 (4.08 g, 29.5 mmol) were added to a flame-dried 250 mL round bottom flask followed by dry acetone (120.0 mL) and MeI (2.0 mL, 32 mmol) at room temperature. A water-jacketed reflux condenser was attached and the reaction was heated under reflux for 12 hours. The reaction was then cooled, filtered, and the solvent was removed under reduced pressure. The brown residue was then resuspended in CH2Cl2, dried over MgSO4, filtered, and condensed. The resulting colorless oil was then purified by flash chromatography (1:9 EtOAc:hexanes) to provide 6 (0.690 g, 3.25 mmol, 99%) as a colorless oil.

Workup

  1. additionwere added to a flame-dried 250 mL round bottom flask
  2. customA water-jacketed reflux condenser was attached
  3. temperaturethe reaction was heated
  4. temperatureunder reflux for 12 hours
  5. temperatureThe reaction was then cooled
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customcondensed
  11. customThe resulting colorless oil was then purified by flash chromatography (1:9 EtOAc:hexanes)

Sources & evidence

ORD record
ord-65e884d6238940ba9ddbbe4560a21a9a
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

Loading…