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

HRID 1098708

Reaktionsgleichung

Reaktionsgleichung von HRID 1098708
[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 42.206,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of paracetamol (250 gm, 1.654 mmol), anhydrous K2CO3 (800 gm, 5.789 mmol) and sodium iodide (17 g, 113 mmol) in anhydrous acetone (5 L) was added methyl 6-bromohexanoate (470 g, 2.25 mmol) and refluxed for 60 hours. Acetone was distilled off and water (3 L) was added. Crude 15 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 15 (195 g, 66%) as a white powder with an m.p between 96.4-98.8° C.

Aufarbeitung

  1. temperaturerefluxed for 60 hours
  2. distillationAcetone was distilled off
  3. additionwater (3 L) was added
  4. filtrationCrude 15 was filtered
  5. customdried
  6. customrecrystallised from a mixture of chloroform:hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-3df0c70905d54054b18f10a499e3e41f
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143325B2

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