Acetaminophen → 2-(4-Acetylamino-phenoxy)-propionic acid methyl ester

HRID 501834

Reaktionsgleichung

Reaktionsgleichung von HRID 501834
[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+].Cl[CH:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23]>CC(C)=O>[CH3:25][O:24][C:22](=[O:23])[CH: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)[CH3:26]

Komponenten

6

Edukt 4

HCID 1983AcetaminophenHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 28659Methyl 2-chloropropionate

Produkt 1

HCID 549413982-(4-Acetylamino-phenoxy)-propionic acid methyl esterAusbeute 27.257,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of paracetamol (150 g, 992 mmol), anhydrous K2CO3 (540 kg, 3.91 mol) and sodium iodide (18 gm, 120 mmol) in anhydrous acetone (3 L) was added methyl 2-chloropropionate (180 g, 1.469 mmol) and refluxed for 80 hours. The acetone was distilled off and water (3 L) was added. Crude 8 was extracted into chloroform, dried over Na2SO4, distilled and hexane (750 ml) was added. The solids were then filtered and recrystallised in methanol to give pure 8 (95 g, 40.4%) as a white powder with an m.p between 96.5-98.2° C.

Aufarbeitung

  1. temperaturerefluxed for 80 hours
  2. distillationThe acetone was distilled off
  3. additionwater (3 L) was added
  4. extractionCrude 8 was extracted into chloroform
  5. dry with materialdried over Na2SO4
  6. distillationdistilled
  7. additionhexane (750 ml) was added
  8. filtrationThe solids were then filtered
  9. customrecrystallised in methanol

Quellen und Nachweise

ORD-Eintrag
ord-f42374ae3f954396ab58355aaaede034
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772352B2

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