Hydrochloric Acid → 1,4-Anthraquinone

HRID 546802

Reaktionsgleichung

Reaktionsgleichung von HRID 546802
[CH:1]1[CH:2]=[CH:3][C:4]2[C:15](=O)[C:14]3[C:9](=[C:10]([OH:18])[CH:11]=[CH:12][C:13]=3[OH:17])[C:7](=O)[C:5]=2[CH:6]=1.[BH4-].[Na+].Cl>CO>[C:13]1(=[O:17])[C:14]2[C:9](=[CH:7][C:5]3[C:4]([CH:15]=2)=[CH:3][CH:2]=[CH:1][CH:6]=3)[C:10](=[O:18])[CH:11]=[CH:12]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6688QuinizarinHCID 4311764Sodium borohydride

Produkt 1

HCID 694571,4-AnthraquinoneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of quinizarin (10.00 g, 42.0 mmol, 1 molar equivalent) in methanol (200 mL) cooled to −0° C. was added sodium borohydride (6.38 g, 169.0 mmol, 4 molar equivalent). The resulting mixture was stirred at −0° C. for 2 h. A solution of 5M hydrochloric acid (150 mL) was then added dropwise to the reaction mixture at −0° C. The precipitated orange solid was filtered, washed twice with water, and dried under vacuum. Purification by column chromatography on silica gel (eluent: dichloromethane) gave the title compound as yellow needles (5.9 g, 68%). 1H NMR (300.13 MHz, CDCl3) (ppm) 7.08 (s, 2H) 7.68-7.72 (m, 2H) 8.05-8.10 (m, 2H) 8.63 (s, 2H).

Aufarbeitung

  1. filtrationThe precipitated orange solid was filtered
  2. washwashed twice with water
  3. customdried under vacuum
  4. customPurification by column chromatography on silica gel (eluent: dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-771fb0fada4f471bb06c313fb4a3c455
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935960B2

Verknüpfte Notizen

Wird geladen…