Isopropyl iodide → 3-isopropoxynitrobenzene

HRID 1461359Notes

Reaction equation

HRID 1461359 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH:11](I)([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:11]([O:10][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 121238953-isopropoxynitrobenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Nitrophenol (50.0 g, 360 mmol), isopropyl iodide (76.19 g, 450 mmol), and potassium carbonate (60 g) were combined and refluxed under nitrogen overnight in 400 ml of acetone. The reaction mixture was cooled, and the solvent was removed in vacuo . The reaction was combined with about 300 ml of water and thereafter extracted with four 100 ml portions of ethyl acetate. The ethyl acetate extracts were combined and washed twice with lN sodium hydroxide and brine, dried over anhydrous sodium sulfate, and evaporated to provide 56 g (86%) of 3-isopropoxynitrobenzene as a clear yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was removed in vacuo
  3. extractionextracted with four 100 ml portions of ethyl acetate
  4. washwashed twice with lN sodium hydroxide and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-3358ad1dec7149cf805b6514fcd9bc1e
Source dataset
uspto-grants-1991_12
Patent number
US05075313

Reaction notes

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