Chloroprene → 2-Chloro-1,4,4a,12a-tetrahydrotetracene-5,6,11,12-tetrone

HRID 261157

Reaktionsgleichung

Reaktionsgleichung von HRID 261157
[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]3[C:17](=[O:18])[CH:16]=[CH:15][C:13](=[O:14])[C:10]=3[C:11](=[O:12])[C:4]2=[CH:3][CH:2]=1)=[O:8].[CH2:19]=[CH:20][C:21]([Cl:23])=[CH2:22]>C(O)(=O)C.CCOCC>[Cl:23][C:21]1[CH2:22][CH:16]2[CH:15]([C:13](=[O:14])[C:10]3[C:11](=[O:12])[C:4]4[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=4[C:7](=[O:8])[C:9]=3[C:17]2=[O:18])[CH2:19][CH:20]=1

Komponenten

5

Edukt 2

HCID 31369ChloropreneHCID 1371691,4,9,10-Anthradiquinone

Produkt 1

HCID 203952152-Chloro-1,4,4a,12a-tetrahydrotetracene-5,6,11,12-tetroneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Quinizarinquinone (I) (1.0 g, 4.2 mmol) and chloroprene (1.12 g, 12.6 mmol) were dissolved in acetic acid (6 ml, glacial) and stirred at ambient temperature under nitrogen for 2.5 days. The reaction mixture was then diluted with ether (25 ml), the reaction mixture filtered, the retained precipitate washed with ether and dried under reduced pressure in the presence of phosphorus pentoxide to yield 9-chloro-6a,7,10,10atetrahydro-5,6,11,12-naphthacenetetraone (II) (988 mg, 72%). Recrystalization (chloroform-ether) gave the foregoing compound in analytical purity m.p. 221°-222° C.,

Aufarbeitung

  1. filtrationthe reaction mixture filtered
  2. washthe retained precipitate washed with ether
  3. dry with materialdried under reduced pressure in the presence of phosphorus pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-5bde6b4aee144e2193ad5df9b73ef4be
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04164503

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