4-Nitrophenol → 2-(4-Nitrophenoxy)ethanol

HRID 856722Notes

Reaction equation

HRID 856722 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][OH:20]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][CH2:19][OH:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 853812-(4-Nitrophenoxy)ethanolYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-nitrophenol (10 g) was dissolved in DMF (100 ml), potassium carbonate (12.9 g) and 2-bromoethanol (10.8 g) were added to the mixture, and the mixture was stirred for 16 hours at 90° C. After cooling to room temperature, the mixture was filtered, and the solvent was removed under reduced pressure. The obtained residue was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 2-(4-nitrophenoxy)ethanol (7.8 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. additionThe obtained residue was added to water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5b1b8919922049d29d0e33fd5102cb8b
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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