4-Nitrophenol → HCID 13049719, compound

HRID 1744513Notes

Reaction equation

HRID 1744513 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[CH:18]([CH3:20])[CH3:19].CN(C)C=O>O>[CH2:17]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH:18]([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium Carbonate

Product 1

HCID 13049719HCID 13049719, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-Nitrophenol (177 g), potassium carbonate (177 g) and isobutyl bromide (190 g) were added to dimethylformamide (500 ml) and the mixture was stirred at 90° C. for 4 h. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The obtained oily substance was distilled under reduced pressure to give 4-isobutoxynitrobenzene (203 g), boiling point: 125° C./0.15 mmHg

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. distillationThe obtained oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-3b07268594ea42fda26d3c521c025615
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

Loading…