Ammonia → 2-Methoxy-1,3,4-trimethylbenzene

HRID 439866Notes

Reaction equation

HRID 439866 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[C:11](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.N>C(#N)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 170162,3,6-Trimethylphenol

Product 1

HCID 5916042-Methoxy-1,3,4-trimethylbenzeneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 50 g (0.367 mol) of 2,3,6-trimethylphenol, 55 g (0.4 mol) of potassium carbonate and 36 ml (0.38 mol) of dimethylsulphate in 500 ml of acetonitrile was heated under reflux overnight. 35 ml of conc. aqueous ammonia was then added, and the mixture refluxed for 1 hour. After filtration and evaporation, the residue was taken up in ether and washed twice with NaOH-solution and twice with NaHCO3 -solution. Drying (MgSO4) and evaporation gave 50.8 g (92%) of the product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperaturethe mixture refluxed for 1 hour
  4. filtrationAfter filtration and evaporation
  5. washwashed twice with NaOH-solution and twice with NaHCO3 -solution
  6. customDrying
  7. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-6bd5b41b971946c2a9b8e90b10a966fe
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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