2-Chloroanthraquinone → 2-Methoxyanthraquinone

HRID 931873

Reaktionsgleichung

Reaktionsgleichung von HRID 931873
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH3:18][O-:19].[Na+]>CN(C)C=O.CO>[CH3:18][O:19][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 85532-ChloroanthraquinoneHCID 10942334Sodium Methoxide

Produkt 1

HCID 186462-Methoxyanthraquinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

First, the intermediate 2-methoxy-9,10-anthraquinone was prepared. A solution of 2-chloro-9,10-anthraquinone (10.08 g, 42 mmol) in 100 mL of N,N-dimethylformamide was treated with 25 mL of 25% sodium methoxide in methanol. The stirred reaction mixture was heated in a 120° C. oil bath for 6 h under nitrogen, then cooled to ambient. The product was precipitated into aqueous HCl (0.5 M, 250 mL), collected, washed with water and dried. The product was purified by recrystallization from a mixture of toluene and heptane to provide 1.6 g (16%) of a light yellow solid. This intermediate was characterized by 1H NMR: (300 MHz, CDCl3) δ 4.00 (s, 3H), 7.28 (d, 1H), 7.29 (d, 1H), 7.70 (m, 2H), 8.26 (s, 1H), 8.30 (m, 2H).

Aufarbeitung

  1. customThe stirred reaction mixture
  2. temperaturecooled
  3. customThe product was precipitated into aqueous HCl (0.5 M, 250 mL)
  4. customcollected
  5. washwashed with water
  6. customdried
  7. customThe product was purified by recrystallization from a mixture of toluene and heptane

Quellen und Nachweise

ORD-Eintrag
ord-601ab51f2a804464a2c4b8ecaac37685
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09298088B2

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