Water → 1-Methoxy-2-methyl-4-nitrobenzene

HRID 881610Notes

Reaction equation

HRID 881610 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[C:12](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[CH3:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 74422-Methyl-4-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 6435201-Methoxy-2-methyl-4-nitrobenzeneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-hydroxy-2-methyl-4-nitrobenzene (1.0 g) in N,N-dimethylformamide (10 mL) were added potassium carbonate (1.8 g) and iodomethane (1.3 g) at room temperature and this mixture was stirred at the same temperature for 24 hours. This reaction mixture was poured into water and this resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.95 g).

Workup

  1. extractionthis resulting mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-db666ccc74d345849e3e12763390b140
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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