1,4-Anthraquinone → 2-Benzylthionaphthacene-5,12-dione

HRID 1084469

Reaktionsgleichung

Reaktionsgleichung von HRID 1084469
[CH2:1]([S:8][C:9]1[CH:14]=[CH:13]O[C:11](=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(=[O:31])[C:29]2[C:20](=[CH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19](=[O:30])[CH:18]=C1>C1C(Cl)=CC=C(Cl)C=1.O=[Mn]=O>[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][C:18]2[C:19](=[O:30])[C:20]3[C:29](=[CH:28][C:27]4[C:22]([CH:21]=3)=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:16](=[O:31])[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 694571,4-AnthraquinoneHCID 146427864-Benzylthio-2-oxo-2H-pyran

Produkt 1

HCID 200635452-Benzylthionaphthacene-5,12-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 46851,4-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 0.27 g (0.0012 mol) of 4-benzylthio-2-oxo-2H-pyrane, 0.25 g (0.0012 mol) of 1,4-anthraquinone and 0.10 g (0.0012 mol) of MnO2 in 5 ml of dichlorobenzene is heated for 24 hours under reflux (180° C.), then cooled and chromatographed over silica gel. Using cyclohexane as eluant, dichlorbenzene is first extracted, then the crude product is chromatographed with CH2Cl2. The pre-purified product is chromatographed once more, using CH2Cl2 as eluant, and the solvent is removed by evaporation. Yield: 0.09 g (20%). Melting point: 200°-203° C.

Aufarbeitung

  1. temperatureis heated for 24 hours
  2. temperaturecooled
  3. customchromatographed over silica gel
  4. extractionUsing cyclohexane as eluant, dichlorbenzene is first extracted
  5. customthe crude product is chromatographed with CH2Cl2
  6. customThe pre-purified product is chromatographed once more
  7. customthe solvent is removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-31ac7a23f62340e896052fd1f43801c3
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05004814

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