Ethyl bromoacetate → Ethyl 2-(4-nitrophenoxy)acetate

HRID 226607

Reaktionsgleichung

Reaktionsgleichung von HRID 226607
[N+:1]([C:4]1[CH:5]=[C:6](O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=[O:12].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:12][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Produkt 1

HCID 308938Ethyl 2-(4-nitrophenoxy)acetateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A dry reaction flask equipped with a reflux condenser, N2 inlet and a magnetic stirring bar was charged with 3-nitrophenol (76.45 g, 550 mmol), K2CO3 (76.45 g, 550 mmol) and dry acetone (500 mL) under N2 atmosphere. To this at room temperature was added ethyl bromoacetate (55.44 mL, 500 mmol) over a period of 15 min. The reaction mixture was refluxed for 16 h, cooled and poured over ice-water (4 Kg). The resulting aqueous solution was extracted with CH2Cl2 (3×500 mL), dried over anhydrous Na2SO4 and solvent was removed to obtain 103 g (92%) of the desired ethyl 4-nitrophenoxyacetate.

Aufarbeitung

  1. customA dry reaction flask
  2. customequipped with a reflux condenser, N2 inlet and a magnetic stirring bar
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. temperaturecooled
  5. extractionThe resulting aqueous solution was extracted with CH2Cl2 (3×500 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customwas removed

Quellen und Nachweise

ORD-Eintrag
ord-c711f8efb704401dbf23ab4d9e5fd6eb
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557210B2

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