Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 638705

Reaktionsgleichung

Reaktionsgleichung von HRID 638705
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)[CH3:24]

Komponenten

5

Edukt 3

HCID 1983AcetaminophenHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Produkt 1

HCID 309738Ethyl 2-(4-acetamidophenoxy)acetateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of Paracetamol (300 g, 1.984 mol), and anhydrous K2CO3 (1.80 Kg, 7.814 mmol) in anhydrous acetone (3 liters) was added ethyl bromoacetate (452 gr, 2.7 mol) and refluxed for 16 hours. Acetone was distilled off and water (5 liter) was added. Crude 13 was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 13 (377 g, 80%) as a white shining powder. The melting point was found to be 104.2-106.2° C.

Aufarbeitung

  1. temperaturerefluxed for 16 hours
  2. distillationAcetone was distilled off
  3. additionwater (5 liter) was added
  4. filtrationCrude 13 was filtered
  5. customdried
  6. customrecrystallised from a mixture of toluene:hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-034d4d086e5c4ec694ca59999af611f7
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691364B2

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