Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 83773

Reaktionsgleichung

Reaktionsgleichung von HRID 83773
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:8]([C:12]1[CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)[C:9]([CH3:11])=[O:10].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:16][C:15]1[CH:14]=[CH:13][C:12]([NH:8][C:9](=[O:10])[CH3:11])=[CH:18][CH:17]=1)[CH3:7]

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

Ethyl bromoacetate (452 g, 2.7 mol.) was added to a mixture of paracetamol (300 g, 1.984 mol) and anhydrous K2CO3 (1.80 kg, 7.814 mmol) in anhydrous acetone (3 L) and refluxed for 16 hours. Acetone was distilled and water (5 L) was added. Crude 1 was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 1 (377 grams, 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
  3. additionwater (5 L) was added
  4. filtrationCrude 1 was filtered
  5. customdried
  6. customrecrystallised from a mixture of toluene:hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-9345771dbcee4f08a6d77263cf5b208c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846845B2

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