Water → 1-Chloro-4-ethoxy-2-nitrobenzene

HRID 1275679

Reaction equation

HRID 1275679 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12](I)[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH3:13])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 2407341-Chloro-4-ethoxy-2-nitrobenzeneYield 94.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-3-nitrophenol (5.21 g, 30 mmol) in acetone (60 ml) were added ethyl iodide (5.94 g, 38 mmol) and potassium carbonate (4.53 g, 33 mmol), followed by stirring at 50° C. for 5 hours. After allowing to stand overnight, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [eluent; ethyl acetate-hexane (1:4)] to give the title compound (5.72 g).

Workup

  1. waitto stand overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution and dried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [eluent; ethyl acetate-hexane (1:4)]

Sources & evidence

ORD record
ord-f22391096a7a4478923087fc634a3098
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Linked notes

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