4-Aminobenzoic Acid → 2,6-Di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-l-one

HRID 1440408

Reaktionsgleichung

Reaktionsgleichung von HRID 1440408
[C:1]([C:5]1[C:6](=[O:16])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:9](=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.B(F)(F)F>O1CCCC1>[C:1]([C:5]1[C:6](=[O:16])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:9](=[N:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 9784-Aminobenzoic AcidHCID 6356Boron trifluorideHCID 128672,6-Di-t-butyl-p-benzoquinone

Produkt 1

HCID 152945432,6-Di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-l-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 22 g (0.10 mole) of 2,6-di(tertiary-butyl)-p-benzoquinone, 13.7 g (0.10 mole) of 4-aminobenzoic acid, 175 ml of tetrahydrofuran and 1 ml of boron trifluoride: diethyl ether complex was heated on a steam bath for 1.25 hours. The mixture was allowed to cool to about 20° C. over 16 hours under a nitrogen atmosphere. Evaporation provided a solid which was washed with hexane and recrystallized from ethanol to provide orange solid 2,6-di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-1-one, m.p. 305°-309° C. Analysis: Calculated for C21H25NO3 : % C, 74.3; % H, 7.4; % N, 4.1; Found: % C, 74.2; % H, 7.4; % N, 4.1.

Aufarbeitung

  1. temperaturediethyl ether complex was heated on a steam bath for 1.25 hours
  2. customEvaporation
  3. customprovided a solid which
  4. washwas washed with hexane
  5. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-40e186cfbba446aaa6d652929e600e3a
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498745

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