Dimethylformamide → 2-(2-(2-(3-Nitrophenoxy)ethoxy)ethoxy)ethanol

HRID 5048

Reaction equation

HRID 5048 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31]>O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 788712-(2-(2-Chloroethoxy)ethoxy)ethanol

Product 1

HCID 197977512-(2-(2-(3-Nitrophenoxy)ethoxy)ethoxy)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

While stirring a mixture of 27.8 g of m-nitrophenol, 120 ml of N,N-dimethylformamide, and 25 g of potassium carbonate at 80° C., 37 g of 2-(2-(2-chloroethoxy)ethoxy)-ethanol was added dropwise to the mixture. After stirring the mixture for one hour at 80° C., 200 ml of ethyl acetate and 200 ml of water were added to the reaction mixture and the ethyl acetate layer was extracted. The ethyl acetate layer was washed with 200 ml of water and concentrated to remove ethyl acetate to provide 2-(2-(2-(3-nitrophenoxy)ethoxy)ethoxy)ethanol (1-A).

Workup

  1. stirringAfter stirring the mixture for one hour at 80° C.
  2. extractionthe ethyl acetate layer was extracted
  3. washThe ethyl acetate layer was washed with 200 ml of water
  4. concentrationconcentrated
  5. customto remove ethyl acetate

Sources & evidence

ORD record
ord-90395268b2774bc9b14694b06a459c4d
Source dataset
uspto-grants-1993_09
Patent number
US05243004

Linked notes

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