Water → 3-isopropoxynitrobenzene

HRID 1493617Notes

Reaction equation

HRID 1493617 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].I[CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:13][CH:12]([O:10][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodide2×HCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 121238953-isopropoxynitrobenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-nitrophenol (20 g; 144 mmol), 2-iodopropane (21.45 m 36.6 g; 216 mmol) and potassium carbonate (23.8 g; 172 mmol) in dimethylformamide (100 ml) was stirred at 50° for 2 h and then the temperature was increased to 70° for a further 2 h. More 2-iodopropane (7.15 ml; 72 mmol) was added and stirring at 70° continued for a further 1.5 h whereupon the mixture was poured into water (400 ml) and extracted with ethyl acetate (2×400 ml). The combined organic extracts were washed with sodium hydroxide (300 ml), then saturated brine (300 ml), dried and evaporated. The residue was chromatographed on silica (675 g) using petroleum ether (40°-60°)-ethyl acetate (10:1) as eluant to give the title compound (Intermediate 43; 22.37 g; 86%) as a yellow oil.

Workup

  1. temperaturethe temperature was increased to 70° for a further 2 h
  2. stirringstirring at 70°
  3. waitcontinued for a further 1.5 h whereupon the mixture
  4. extractionextracted with ethyl acetate (2×400 ml)
  5. washThe combined organic extracts were washed with sodium hydroxide (300 ml)
  6. dry with materialsaturated brine (300 ml), dried
  7. customevaporated
  8. customThe residue was chromatographed on silica (675 g)
  9. custompetroleum ether (40°-60°)-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-b104581abd3d4d22b44691a4ad3a1872
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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