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Water → Ibuprofen Piconol

HRID 26455
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 26455
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[CH2:9]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20](Cl)=[O:21])=[CH:15][CH:14]=1)[CH:10]([CH3:12])[CH3:11].C(N(CC)CC)C.O>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:20](=[O:21])[CH:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:14][CH:15]=1)[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 11474PiconolHCID 595157alpha-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Produkt 1

HCID 3673Ibuprofen PiconolAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 2.2 g of 2-pyridinemethanol in 20 ml of tetrahydrofuran were added 3 g of 2-(4-isobutylphenyl)propionic acid chloride and subsequently 2.7 g of triethylamine, and the mixture was reacted at room temperature for 2 hours. After the reaction was complete, the crystals produced were removed by filtration. The filtrate was freed of solvent by distillation to leave a residue, to which was added water. The resulting mixture was extracted with ether. The ether extract was dehydrated and freed of ether by distillation. The oily residue thus obtained was distilled in vacuo to give 3.5 g of 2-(4-isobutylphenyl)propionic acid-2-pyridylmethyl ester as a pale yellow oil, boiling at 138°-140° C./0.15 mmHg. Mass spectrum: parent ion 297 m/e.

Aufarbeitung

  1. customthe mixture was reacted at room temperature for 2 hours
  2. customthe crystals produced
  3. customwere removed by filtration
  4. distillationThe filtrate was freed of solvent by distillation
  5. customto leave a residue
  6. extractionThe resulting mixture was extracted with ether
  7. extractionThe ether extract
  8. distillationfreed of ether by distillation
  9. customThe oily residue thus obtained
  10. distillationwas distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-54cc47a78449481494b15c343d1d17db
Quelldatensatz
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04150137

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