Quinizarin → 1,4,9,10-Anthradiquinone

HRID 2397267

Reaktionsgleichung

Reaktionsgleichung von HRID 2397267
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][CH:3]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[C:2]1(=[O:1])[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](=[O:18])[CH:4]=[CH:3]1

Komponenten

4

Edukt 2

HCID 6688QuinizarinHCID 178418268HCID 178418268, Verbindung

Produkt 1

HCID 1371691,4,9,10-AnthradiquinoneAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1,4-dihydroxyanthraquinone (10.0 g), lead tetraacetate (20 g) and acetic acid (25 ml) was ground together in mortar and pestle for 10 minutes at 25°. The reaction mixture was filtered and the solid washed with acetic acid, water, and ether. The red solid was taken up in a large volume of aceton (700 ml), the solution filtered through Celite, dried over sodium sulfate and evaporated under reduced pressure to give 1,4,9,10 anthradiquinone (8.2 g, 81% yield) as a brown solid. m.p. 213°-215° C. (benzene/pet. ether) lit m.p. 211°-213° NMR (CDCl3) δ8.2-7.8 (m, 4H aryl), 6.88 (s, 2H); IR 5.95, 610 (sh), 6.15 (sh), 6.3μ.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe solid washed with acetic acid, water, and ether
  3. filtrationthe solution filtered through Celite
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fb0ebff14f294ab8bc22ff31b17d8c84
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04021457

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