2-Methyl-4-nitrophenol → HCID 68752044, compound

HRID 1963762Notes

Reaction equation

HRID 1963762 reaction equation
C[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12](=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH:21]=[CH2:22]>C(#N)C>[CH2:19]([O:11][C:3]1[CH:2]=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([CH3:12])[CH:4]=1)[CH2:20][CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 74422-Methyl-4-nitrophenolHCID 11430Potassium CarbonateHCID 21241Homoallyl bromide

Product 1

HCID 68752044HCID 68752044, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (50 mL) solution of 2-methyl-4-nitrophenol (3.05 g; 19.9 mmol) and potassium carbonate (4.27 g; 30.9 mmol), 4-bromo-1-butene (4.02 g; 29.8 mmol) was added, and the mixture was refluxed and then reacted for 12 hours. After completion of the reaction, the solution was filtrated by Celite, and then 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)-2-methylnitrobenzene (1c) (2.61 g, 63% of yield, a light yellow oil) represented by the following formula.

Workup

  1. temperaturethe mixture was refluxed
  2. customreacted for 12 hours
  3. customAfter completion of the reaction
  4. filtrationthe solution was filtrated by Celite
  5. concentrationfiltrate 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-9f221d2e4a7c441c862d2f3fd5e98277
Source dataset
uspto-grants-2013_04
Patent number
US08415451B2

Reaction notes

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