4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 55487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 55487
[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-73f060dfe6de4044aca39bfe30d68e8e
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624935

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