Aluminum(III) Chloride → Ibuprofen, (+-)-

HRID 27807

Reaktionsgleichung

Reaktionsgleichung von HRID 27807
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:22])[C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.[N+](C)([O-])=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:22])[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

7

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 104246622-(p-Isobutylphenyl)propionic acid benzyl ester

Produkt 1

HCID 3672Ibuprofen, (+-)-Ausbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittelHCID 6375NitromethaneLösungsmittelHCID 7519AnisoleLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of benzyl 2-p-isobutylphenylpropionate (3 g) in methylene chloride (18 ml) are added a solution of aluminum chloride (4 g) in nitromethane (50 ml) and anisole (3 ml) at 0° C., and the mixture is stirred at room temperature for 6 hours. The reaction mixture is diluted with ethyl acetate, washed with hydrochloric acid and water, dried and evaporated. The residue is recrystallized with n-hexane to give 2-p-isobutylphenylpropionic acid (186 mg) melting at 75°-77.5° C. Yield 91%.

Aufarbeitung

  1. washwashed with hydrochloric acid and water
  2. customdried
  3. customevaporated
  4. customThe residue is recrystallized with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-fe55e9d7d722407189fc1a59ff07f4bc
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04223132

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