Water → 2,3,5-Trimethylanisole

HRID 1632465Notes

Reaction equation

HRID 1632465 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[CH3:11]I.[H-].[Na+].O>CS(C)=O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 127692,3,5-TrimethylphenolHCID 24758Sodium hydride

Product 1

HCID 885552,3,5-Trimethylanisole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 100 ml of dimethyl sulfoxide were dissolved 10 g of 2,3,5-trimethylphenol and 10.4 ml of methyl iodide and the solution was ice-cooled. To this solution was added 5.6 g of 60% oily sodium hydride and the mixture was stirred for 10 hours. Water was added and the resulting mixture was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off to give an oily substance. Yield 12.9 g (quantitative).

Workup

  1. temperaturecooled
  2. extractionthe resulting mixture was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off
  6. customto give an oily substance

Sources & evidence

ORD record
ord-da344e2082944f688dd0911bdaff6877
Source dataset
uspto-grants-1984_10
Patent number
US04476051

Reaction notes

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