Pyridine → 4,5-Bisbutyryloxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

HRID 12939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12939
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1.[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25].C([O:31][CH2:32][CH3:33])(=O)C.ClCCl.N1C=CC=[CH:39][CH:38]=1>O>[C:22]([O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[O:17][C:32](=[O:31])[CH2:33][CH2:38][CH3:39])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1)(=[O:26])[CH2:23][CH2:24][CH3:25]

Komponenten

7

Edukt 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 10168Rhein

Produkt 1

HCID 112931694,5-Bisbutyryloxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acidAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4,5-Dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (3.0 g) was suspended in pyridine (100 ml) and stirred at RT for 30 mins. Butyryl chloride was added (3.6 g, 5 equiv.) to give a clear reaction mixture which was stirred at RT over the weekend. The reaction mixture was reduced to a smaller volume and quenched with 2M HCl (200 ml), adjusting the pH to pH 2. An orange solid was isolated by filtration. This solid was slurried in water (30 ml) followed by ethyl acetate (30 ml) and dichloromethane (30 ml), and isolated by filtration as a yellow solid (2.0 g, 45%).

Aufarbeitung

  1. customto give a clear reaction mixture which
  2. stirringwas stirred at RT over the weekend
  3. customquenched with 2M HCl (200 ml)
  4. customAn orange solid was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-169ad7e3e7fa4c7ca57b982259a2dbc0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728035B2

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