4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 482515

Reaktionsgleichung

Reaktionsgleichung von HRID 482515
[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>[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

5

Edukt 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 56 g of 4-nitrophenol, 90 g of methyl bromoacetate, 100 g of potassium carbonate and 500 ml of dimethylformamide was stirred at room temperature for 2 days. At the end of this time, the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with water and the aqueous mixture 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 triturated with hexane to give 63.3 g of the title compound, melting at 98-99° C.

Aufarbeitung

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionThe resulting residue was mixed with water
  3. extractionthe aqueous mixture 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 triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-9aafb63e5ac64ee4bfd4335bbfc2c594
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05798375

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