Water → 4-Tert-butyl-2-nitrobenzoic acid

HRID 1644198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1644198
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#C)=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(#N)C.I(O)(=O)(=O)=[O:20].[OH2:24]>C(Cl)(Cl)(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:20])=[O:24])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 6342AcetonitrileHCID 65185Metaperiodic acidHCID 580162084-Tert-butyl-1-ethynyl-2-nitrobenzene

Produkt 1

HCID 2573264-Tert-butyl-2-nitrobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6093376Ruthenium trichloride hydrateKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

4-tert-Butyl-1-ethynyl-2-nitro-benzene (1.662 g, 8.176 mmol) was dissolved in 20 mL carbon tetrachloride, 20 mL acetonitrile, and 40 mL water. Periodic acid (9.322 g, 40.89 mmol) was added followed by ruthenium(III)chloride hydrate (85 mg, 0.41 mmol). After stirring of 90 minutes, the resulting mixture was diluted with water and extracted with three portions of dichloromethane. The combined dichloromethane layers wee dried over anhydrous MgSO4, and concentrated in vacuo to yield 4-tert-Butyl-2-nitro-benzoic acid (1.924 g, 86.19 mmol).

Aufarbeitung

  1. extractionextracted with three portions of dichloromethane
  2. dry with materialThe combined dichloromethane layers wee dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4e7e177bb8104ba1bf09655ed606f506
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124604B2

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