4-Nitrophenol → Ethyl 2-(4-nitrophenoxy)acetate

HRID 507932Notes

Reaction equation

HRID 507932 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:17]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-nitrophenol (10 g, 71.9 mmol), ethyl bromoacetate (13.5 g, 80.8 mmol) and potassium carbonate (12.0 g, 86.8 mmol) in N,N-dimethylformamide (100 mL) was stirred at room temperature for 18 hr. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed successively with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with diethyl ether-hexane to give the title compound (16.0 g, yield 99%) as colorless needle crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe obtained crystals were washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-bd7cdb32afde4a5288344115f0499d5b
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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