4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 356283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356283
[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][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Produkt 1

HCID 700522Methyl (4-nitrophenoxy)acetateAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 56 g of 4-nitrophenol, 90 g of methyl bromoacetate and 100 g of potassium carbonate in 500 ml of dimethylformamide was stirred at room temperature for 2 days. At the end of this time, the reaction mixture was freed from dimethylformamide by distillation under reduced pressure. The residue thus obtained was diluted with water, after which it was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was crystallized by trituration with hexane, to give 63.3 g of the title compound, melting at 98°-99° C.

Aufarbeitung

  1. distillationAt the end of this time, the reaction mixture was freed from dimethylformamide by distillation under reduced pressure
  2. customThe residue thus obtained
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was crystallized by trituration with hexane

Quellen und Nachweise

ORD-Eintrag
ord-2c4510170c3d41ba8854f8a263df9a9a
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834501

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