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Quinizarin → 1,4-Bis(octyloxy)anthracene-9,10-dione

HRID 1897378
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1897378
[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](O)=[CH:4][CH:3]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[C:28](=[O:31])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:20]([O: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]([O:31][CH2:28][CH2:14][CH2:15][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:4][CH:3]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6688QuinizarinHCID 81401-BromooctaneHCID 11430Potassium Carbonate2×

Produkt 1

HCID 684413171,4-Bis(octyloxy)anthracene-9,10-dioneAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1,4-dihydroxyanthracene-9,10-dione (5.0 g, 20.6 mmol), 1-bromooctane (10.0 g, 51.8 mmol), and potassium carbonate (37 g, 0.268 mol) was mixed in N,N-dimethylformamide and heated at 90° C. for 7 h after which the potassium carbonate was filtered off. The reaction mixture was quenched with water and extracted three times with ether. The ether was then washed three times with 1M HCl, one time with water, and evaporated to give a dark yellow solid. This solid was recrystallised in methanol to yield 1,4-bis(octyloxy)anthracene-9,10-dione (1.81 g, 3.88 mmol) as a yellow solid. 1H-NMR (CDCl3, δ): 0.89 (t, 6H), 1.2-1.4 (m, 16H), 1.53 (m, 4H), 1.93 (m, 4H), 4.10 (t, 4H), 7.30 (s, 2H), 7.71 (m, 2H), 8.16 (m, 2H) MS MALDI-TOF (m/z): 464.328

Aufarbeitung

  1. filtrationwas filtered off
  2. customThe reaction mixture was quenched with water
  3. extractionextracted three times with ether
  4. washThe ether was then washed three times with 1M HCl, one time with water
  5. customevaporated
  6. customto give a dark yellow solid
  7. customThis solid was recrystallised in methanol

Quellen und Nachweise

ORD-Eintrag
ord-7ba812df1b5f4250bdcb8ee5c7bd5b90
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08519037B2

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