2,6-Ditert-butyl-4-(4-nitrophenyl)phenol → 4'-Amino-3,5-di-t-butyl-4-hydroxybiphenyl

HRID 224458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 224458
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[OH:24])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:6]([OH:24])=[C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:8]=2)=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 17349052,6-Ditert-butyl-4-(4-nitrophenyl)phenolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 155988104'-Amino-3,5-di-t-butyl-4-hydroxybiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 50 g. (0.152 mole) of 2,6-di(t-butyl)-4-(4'-nitrophenyl)phenol in 350 ml. of ethyl acetate is reduced with hydrogen gas at about 45 psig in a Paar apparatus using 10 percent palladium on charcoal as catalyst. The mixture is allowed to stand for about 16 hours, filtered, and the filtrate evaporated under vacuum. The residue is cooled, dissolved in ethanol and triturated with water. The resulting off-white solid is recrystallized from petroleum ether to provide 4-(4'-aminophenyl)-2,6-di(t-butyl)phenol, m.p. 113°-114.5° C.

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate evaporated under vacuum
  3. temperatureThe residue is cooled
  4. dissolutiondissolved in ethanol
  5. customtriturated with water
  6. customThe resulting off-white solid is recrystallized from petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-87a7cbb1c0714b4d8e50e8717079c1b5
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04232043

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