Isopropyl iodide → 3-isopropoxynitrobenzene

HRID 2298464Notes

Reaction equation

HRID 2298464 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 K2CO3 (60 g) were combined and heated at reflux under N2 overnight in acetone (400 mL). After solvent removal in vacuo, the residue was partitioned between EtOAc and H2O. The separated organic layer was washed with 1 N NaOH, brine, dried over Na2SO4, and concentrated in vacuo to provide 56 g (86%) of 3-isopropoxynitrobenzene as a clear yellow oil.

Workup

  1. temperatureheated
  2. customAfter solvent removal in vacuo
  3. customthe residue was partitioned between EtOAc and H2O
  4. washThe separated organic layer was washed with 1 N NaOH, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07636d8e6a6d42d09c34c399858e1c18
Source dataset
uspto-grants-2002_12
Patent number
US06492531B1

Reaction notes

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