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Water → 8-Acetoxy-10-chloro-9-hydroxy-1,4-anthracenedione

HRID 620901
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 620901
[Cl:1][C:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9]([OH:17])=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]2=[O:18].O.[O:21]1CC[CH2:23][CH2:22]1>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:22]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[C:9]([OH:17])=[C:8]1[C:3]([C:4](=[O:19])[CH:5]=[CH:6][C:7]1=[O:18])=[C:2]2[Cl:1])(=[O:21])[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 1366779410-Chloro-8,9-dihydroxy-1,4-anthracenedione2×

Produkt 1

HCID 110344498-Acetoxy-10-chloro-9-hydroxy-1,4-anthracenedione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysator
HCID 7918
Acetic Anhydride
Katalysator

Versuchsvorschrift

10-Chloro-8,9-dihydroxy-1,4-anthracenedione (compound 3) (180 mg) was dissolved with stirring in dry tetrahydrofuran (15 ml) at room temperature. Acetic anhydride (20 drops) and pyridine (15 drops) were added to the solution which was then stirred for 48 h. Acidified water was added and the suspension was extracted with dichloromethane. The combined organic layers were dried and evaporated, and the residue was column chromatographed on silica gel 60 (100 g) with chloroform/acetone mixture as the eluant. The major red band gave the product (compound 4) as a red solid (177 mg, 85%).

Aufarbeitung

  1. extractionthe suspension was extracted with dichloromethane
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customchromatographed on silica gel 60 (100 g) with chloroform/acetone mixture as the eluant

Quellen und Nachweise

ORD-Eintrag
ord-c7b4992f2a4d477c879ebddef80de30b
Quelldatensatz
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04822873

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