Water → Ethyl 2-(4-aminophenoxy)acetate

HRID 1290992Notes

Reaction equation

HRID 1290992 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-])=O.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 412616Ethyl 2-(4-aminophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitrophenol (25.0 g, 180 mmol) and ethyl bromoacetate (20.0 ml, 180 mmol) were dissolved in N,N-dimethylformamide (40 ml), and potassium carbonate (27.4 g, 198 mmol) was added. The mixture was stirred at room temperature for 16 hours under a nitrogen atmosphere. The reaction mixture was poured into water (100 ml) and extracted with an equivalent mixture of n-hexane and ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure to quantitatively give 40.5 g of ethyl 4-aminophenoxyacetate as a colorless solid.

Workup

  1. extractionextracted with an equivalent mixture of n-hexane and ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration, low boiling matters
  5. distillationwere distilled away from the filtrate under reduced pressure to quantitatively give 40.5 g of ethyl 4-aminophenoxyacetate as a colorless solid

Sources & evidence

ORD record
ord-d8b9dac449254c31a0b0f37871b31668
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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