4-Nitrophenol → Allyl p-nitrophenyl ether

HRID 1967174Notes

Reaction equation

HRID 1967174 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[C:14]([OH:21])[CH:13]=1.Br[CH2:23][CH:24]=[CH2:25]>C1(C)C=CC=CC=1>[N+:18]([C:17]1[CH:16]=[CH:15][C:14]([O:21][CH2:25][CH:24]=[CH2:23])=[CH:13][CH:12]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 220100Allyl p-nitrophenyl etherYield 79.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium carbonate (49.7 g, 0.36 mol) was added to an N,N-dimethylformamide (250 ml) solution of p-nitrophenol (25.0 g, 0.18 mol) under nitrogen atmosphere and suspended, and 3-bromopropene (21.7 g, 0.18 mol) was dropwise added thereto. After finishing dropwise adding, the solution was stirred at a room temperature for 5 hours, and then extracting practice with diethyl ether was carried out after adding water to the solution. The organic layer was washed with water and then dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue thus obtained was refined by means of silica gel chromatography (eluent solvent: toluene). Toluene was distilled off under reduced pressure, and then the resulting residue was recrystallized from ethanol to obtain allyl p-nitrophenyl ether (25.7 g).

Workup

  1. additionAfter finishing dropwise adding
  2. extractionextracting practice with diethyl ether
  3. additionafter adding water to the solution
  4. washThe organic layer was washed with water
  5. dry with materialdried on anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue thus obtained
  8. distillationToluene was distilled off under reduced pressure
  9. customthe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ae09f0167f604340befd9effffb0f4ca
Source dataset
uspto-grants-2013_04
Patent number
US08420764B2

Reaction notes

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