4-Nitrophenol → HCID 53656183, compound

HRID 1650342Notes

Reaction equation

HRID 1650342 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.Br[CH2:12][CH2:13][CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:12]([O:10][C:3]1[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=1)=[CH:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 53656183HCID 53656183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 500 ml flask equipped with a mechanical stirrer, condenser, thermometer, and heating mantle was charged with p-nitrophenol (30.0 g, 216 mmol), 4-bromo-1-butene (29.1 g, 216 mmol), potassium carbonate (32.8 g, 237 mmol) and DMF (300 ml). The reaction mixture was heated to reflux and stirred for 48 hours. It was then cooled and solvent removed under reduced pressure. The residue was dissolved in 250 ml of methylene chloride and washed repeatedly with water to remove traces of DMF. The methylene chloride layer was dried (MgSO4), filtered, and solvent removed under reduced pressure. The product was used without further purification for the next step. Yield=7.0 g (17%).

Workup

  1. customA 500 ml flask equipped with a mechanical stirrer, condenser
  2. temperaturethermometer, and heating mantle
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. temperatureIt was then cooled
  6. customsolvent removed under reduced pressure
  7. dissolutionThe residue was dissolved in 250 ml of methylene chloride
  8. washwashed repeatedly with water
  9. customto remove traces of DMF
  10. dry with materialThe methylene chloride layer was dried (MgSO4)
  11. filtrationfiltered
  12. customsolvent removed under reduced pressure
  13. customThe product was used without further purification for the next step

Sources & evidence

ORD record
ord-bfb4053a96b04004900e7cc2a70e0edf
Source dataset
uspto-grants-1990_05
Patent number
US04923997

Reaction notes

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