Ethanol → 4-(3,5-Di-tertiary-butyl-4-hydroxyanilino)benzoic acid

HRID 1440411

Reaktionsgleichung

Reaktionsgleichung von HRID 1440411
C(O)C.[C:4]([C:8]1[C:9](=[O:28])[C:10]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:11][C:12](=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)[CH:13]=1)([CH3:7])([CH3:6])[CH3:5].C(=O)([O-])[O-].[K+].[K+]>[Pd].O>[C:4]([C:8]1[CH:13]=[C:12]([CH:11]=[C:10]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:9]=1[OH:28])[NH:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([OH:23])=[O:22])=[CH:19][CH:20]=1)([CH3:7])([CH3:6])[CH3:5]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 152945432,6-Di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-l-one

Produkt 1

HCID 139604064-(3,5-Di-tertiary-butyl-4-hydroxyanilino)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 200 ml of ethanol and 25.0 g (0.0736 mole) of 2,6-di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-1-one and 12 g (0.087 mole) of potassium carbonate warmed on a steam bath was added 1.0 g of palladium on charcoal. The mixture was reduced using a Paar apparatus for 2 hours. The mixture was diluted with 300 ml of water, filtered through celite, and the filtrate acidified with 6N hydrochloric acid. The yellow solid precipitate was collected by filtration to provide 4-[3,5-di(tertiary-butyl)-4-hydroxyanilino]benzoic acid, m.p. 241°-242° C.

Aufarbeitung

  1. temperaturewarmed on a steam bath
  2. customfor 2 hours
  3. filtrationfiltered through celite
  4. filtrationThe yellow solid precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-b998f01c036441d3858b1e5a62193bc3
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498745

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