Acetaminophen → 6-(4-Acetylaminophenoxy)-hexanoic acid methyl ester

HRID 638711

Reaktionsgleichung

Reaktionsgleichung von HRID 638711
[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+].[I-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>CC(C)=O>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1983AcetaminophenHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4170292Methyl 6-Bromohexanoate

Produkt 1

HCID 497644916-(4-Acetylaminophenoxy)-hexanoic acid methyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of Paracetamol (250 g, 1.654 mol), anhydrous K2CO3 (800 g, 5.789 mol) and sodium iodide (17 g, 113 mmol) in anhydrous acetone (5 liters) was added methyl 6-bromohexanoate (470 g, 2.25 mol) and refluxed for 60 hours. Acetone was distilled off and water (3 liter) was added. Crude 19 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 19 (195 g, 66%) as a white powder. The melting point was found to be 96.4-98.8° C. The product was tested by HPLC and found to be 99%+ pure. The structure was confirmed with NMR.

Aufarbeitung

  1. temperaturerefluxed for 60 hours
  2. distillationAcetone was distilled off
  3. additionwater (3 liter) was added
  4. filtrationCrude 19 was filtered
  5. customdried
  6. customrecrystallised from a mixture of chloroform:hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-9fe5ecc39f934331aa93e1d1dc3ab976
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691364B2

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