Dimethylformamide → 4-ethoxy-1-methyl-2-nitrobenzene

HRID 1026246Notes

Reaction equation

HRID 1026246 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].I[CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:13]([O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresol

Product 1

HCID 3503664-ethoxy-1-methyl-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-Methyl-3-nitrophenol (10.0 g) was mixed with iodoethane (10.5 mL), potassium carbonate (13.5 g) and DMF (130 mL), and the obtained mixture was stirred at 60° C. overnight. Water was added to the reaction mixture, and the mixture was extracted twice with diethyl ether. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a yellow oil (11.8 g).

Workup

  1. extractionthe mixture was extracted twice with diethyl ether
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-54f18a8c398147ba8bb7a47f5f051c12
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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