Phloroglucinol → 1,3-dihydroxy-12H-benzo(b)xanthen-12-one

HRID 83107

Reaktionsgleichung

Reaktionsgleichung von HRID 83107
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:15]1([CH:23]=[C:21](O)[CH:20]=[C:18]([OH:19])[CH:17]=1)[OH:16]>[Cl-].[Cl-].[Zn+2].O=P(Cl)(Cl)Cl>[OH:16][C:15]1[C:23]2[C:12](=[O:14])[C:3]3[CH:4]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:10]4=[CH:11][C:2]=3[O:1][C:21]=2[CH:20]=[C:18]([OH:19])[CH:17]=1

Komponenten

5

Edukt 2

HCID 359PhloroglucinolHCID 71043-Hydroxy-2-naphthoic acid

Produkt 1

HCID 107077051,3-dihydroxy-12H-benzo(b)xanthen-12-oneAusbeute 9,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 24813Phosphorus oxychlorideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-hydroxy-2-naphthoic acid (2.0 g, 10.63 mmol), phloroglucinol (1.34 g, 10.63 mmol), ZnCl2 (3.30 g, 24.24 mmol) and POCl3 (40 mL) was stirred under reflux at 80° C. for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and was very slowly added to 1 L of ice water. The resulting solid was allowed to stand (1 d), filtered, washed with water, and then dried under reduced pressure to obtain an ocherous compound. This compound was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give the title compound (289 mg, 9.8%) as a yellow solid.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. custom(1 d)
  3. filtrationfiltered
  4. washwashed with water
  5. customdried under reduced pressure
  6. customto obtain an ocherous compound
  7. customThis compound was separated
  8. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-98e6d9d9540844bd8f0349e988c593d1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846749B2

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