Isopropyl iodide → 3-isopropoxynitrobenzene

HRID 1614201Notes

Reaction equation

HRID 1614201 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 1N 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 1N sodium hydroxide and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-51ade90e52c44e5da986c54eb596e5c7
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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