4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 83778

Reaktionsgleichung

Reaktionsgleichung von HRID 83778
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:18][C:19]([O:21][CH3:22])=[O:20]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 9804-NitrophenolHCID 7295Methyl chloroacetateHCID 11430Potassium Carbonate

Produkt 1

HCID 700522Methyl (4-nitrophenoxy)acetateAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of 4-nitrophenol (100 g, 719 mmol) and anhydrous K2CO3 (400 gm, 2.894 mol) in anhydrous acetone (950 ml) was added methyl chloroacetate (114 g, 1.050 moles) and refluxed for 12 hours. Acetone was distilled off and water (1500 ml) was added. Crude 7 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 7 (110 g, 72.5%) as a white fluffy powder with an m.p between 97-98.4° C.

Aufarbeitung

  1. temperaturerefluxed for 12 hours
  2. distillationAcetone was distilled off
  3. additionwater (1500 ml) was added
  4. filtrationCrude 7 was filtered
  5. customdried
  6. customrecrystallised from a mixture of ethyl acetate:hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-babbe404bc1e4121af8d645fddc011eb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846845B2

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