4-Nitrophenol → 4-(3-Butenyloxy)nitrobenzene

HRID 1963756Notes

Reaction equation

HRID 1963756 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+].Br[CH2:18][CH2:19][CH:20]=[CH2:21]>C(#N)C>[CH2:21]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:20][CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 112177694-(3-Butenyloxy)nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (20 mL) solution of 4-nitrophenol (0.423 g; 3.04 mmol) and potassium carbonate (1.11 g; 8.02 mmol), 4-bromo-1-butene (0.827 g; 6.13 mmol) was added, and the mixture was refluxed and then reacted for 17 hours. After completion of the reaction, the solution was filtrated by Celite, and then the filtrate was concentrated under a reduced pressure. The residue was purified by flash column chromatography using methylene chloride, and then the effluent was concentrated to obtain 4-(3-butenyloxy)nitrobenzene (1) (0.571 g, 97% of yield, a light yellow oil) represented by the following formula.

Workup

  1. temperaturethe mixture was refluxed
  2. customreacted for 17 hours
  3. customAfter completion of the reaction
  4. filtrationthe solution was filtrated by Celite
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customThe residue was purified by flash column chromatography
  7. concentrationthe effluent was concentrated

Sources & evidence

ORD record
ord-8e893467d62f41b6a57c287f23c04925
Source dataset
uspto-grants-2013_04
Patent number
US08415451B2

Reaction notes

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