Methyl iodide → 1-Methoxy-2-methyl-4-nitrobenzene
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-methyl-4-nitrophenol (10.2 g, 67 mmol) in acetonitrile (250 mL) was added potassium carbonate (27.6 g, 200 mmol) and methyl iodide (4.1 mL, 66 mmol). The mixture was stirred at 80° C. for 12 h. After cooling to room temperature, the solid was removed by filtration and the filtrate was evaporated under reduced pressure. The resulting oil was dissolved in dichloromethane (250 mL). The solution was washed with 2N NaOH (aq.) (200 mL), brine (100 mL), dried (Na2SO4), filtered and evaporated to yield 1-methoxy-2-methyl-4-nitrobenzene (9.5 g, 57 mmol, 85%).
Workup
- temperatureAfter cooling to room temperature
- customthe solid was removed by filtration
- customthe filtrate was evaporated under reduced pressure
- dissolutionThe resulting oil was dissolved in dichloromethane (250 mL)
- washThe solution was washed with 2N NaOH (aq.) (200 mL), brine (100 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-79528652a3ac480bb775cdad89ec12fc
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807686B2
Reaction notes
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