Water → 2,3,5-Trimethylanisole

HRID 1154147

Reaction equation

HRID 1154147 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 DMSO were dissolved 10 g of 2,3,5-trimethylphenol and 10.4 ml of methyl iodide. Under ice-cooling, 5.6 g of 60% sodium hydride in oil was added, and the mixture was stirred at room temperature for 10 hours. After addition of water, the extraction with ether was carried out. The ether layer was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent by distillation leaves the oily substance. Yield 12.9 g (quantitative)

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe extraction with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the solvent
  6. distillationby distillation
  7. customleaves the oily substance

Sources & evidence

ORD record
ord-2189fa23ece643879df3626b0fc3c881
Source dataset
uspto-grants-1984_12
Patent number
US04487726

Linked notes

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