Methyl iodide → 4-Methoxyazobenzene

HRID 23567Notes

Reaction equation

HRID 23567 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([N:7]=[N:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[CH:5][CH:6]=1.IC.[C:18](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:18][O:15][C:12]1[CH:11]=[CH:10][C:9]([N:8]=[N:7][C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 155294-Hydroxyazobenzene

Product 1

HCID 169664-Methoxyazobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-phenylazophenol (9.9 g; 50 mmol), iodomethane (7.1 g; 50 mmol), potassium carbonate (6.9 g; 50 mmol), and acetone (100 ml) was refluxed 48 h. After evaporating off the solvent, the residue was dissolved in water (25 ml), diethyl ether (50 ml) and THF (30 ml). The aqueous layer was extracted with ether (3×20 ml) and the combined organic solutions were washed with saturated NaCl solution (1×20 ml) and dried (MgSO4). After filtration and evaporation, the residue was recrystallized from 96% ethanol to give 8.7 g (82%).

Workup

  1. temperaturewas refluxed 48 h
  2. customAfter evaporating off the solvent
  3. dissolutionthe residue was dissolved in water (25 ml)
  4. extractionThe aqueous layer was extracted with ether (3×20 ml)
  5. washthe combined organic solutions were washed with saturated NaCl solution (1×20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration and evaporation
  8. customthe residue was recrystallized from 96% ethanol
  9. customto give 8.7 g (82%)

Sources & evidence

ORD record
ord-fe45e5a362624d65ba6e0a8dbae3e43f
Source dataset
uspto-grants-2005_02
Patent number
US06852749B1

Reaction notes

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