2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,2,3,4,6,11-Hexapropylnaphthacene

HRID 600143

Reaktionsgleichung

Reaktionsgleichung von HRID 600143
[CH2:1]([C:4]1[C:21]2[CH2:20][C:19]3[C:10](=[C:11]([CH2:25][CH2:26][CH3:27])[C:12]4[C:17]([C:18]=3[CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:9][C:8]=2[C:7]([CH2:28][CH2:29][CH3:30])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[CH2:34][CH2:35][CH3:36])[CH2:2][CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:28]([C:7]1[C:8]2[C:21](=[CH:20][C:19]3[C:10]([CH:9]=2)=[C:11]([CH2:25][CH2:26][CH3:27])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]=3[CH2:22][CH2:23][CH3:24])[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]([CH2:34][CH2:35][CH3:36])[C:6]=1[CH2:31][CH2:32][CH3:33])[CH2:29][CH3:30]

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178395091,2,3,4,6,11-Hexapropyl-5,12-dihydrotetracene

Produkt 1

HCID 230670861,2,3,4,6,11-HexapropylnaphthaceneAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5,12-Dihydro-1,2,3,4,6,11-hexapropylnaphthacene (0.503 g, 1.04 mmol), 2,3-dichloro-5,6-dicyanobenzoquinone (0.260 g, 1.14 mmol) and 1,4-dioxane (3 ml) were charged in a reactor. The mixture was refluxed for 24 hours. After cooling, the precipitates were removed by filtration. The solvent in the mixture was removed in vacuum followed by recrystallization from chloroform/methanol. The orange red title compound (0.112 g) was obtained. The NMR yield was 36% and the isolation yield was 22%.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. customthe precipitates were removed by filtration
  4. customThe solvent in the mixture was removed in vacuum
  5. customfollowed by recrystallization from chloroform/methanol

Quellen und Nachweise

ORD-Eintrag
ord-5b21c6cd30d14b6eabb6f23e4e444a11
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07901594B2

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