Ammonia → 1,8-Dichloroanthracene

HRID 489501

Reaktionsgleichung

Reaktionsgleichung von HRID 489501
[Cl:1][C:2]1[C:15]2[C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Cl:17])[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N>[Zn]>[Cl:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[C:12]([Cl:17])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 67081,8-Dichloroanthraquinone

Produkt 1

HCID 6188901,8-Dichloroanthracene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

25 g (91 mmol) of 1,8-dichloroanthraquinone and 65 g (1 mol) of Zn dust were suspended in 1 l of a 20% strength by weight aqueous ammonia solution and the mixture was refluxed for 3 hours. After cooling to room temperature, the solid was separated off via a Büchner funnel. The aqueous phase was extracted three times with 150 ml each time of dichloromethane; the solid was extracted a number of times with dichloromethane while being treated with ultrasound. The combined organic phases were dried over magnesium sulfate and freed of the solvent on a rotary evaporator. The solid, whitish yellow residue was suspended in 600 ml of propanol and 65 ml of 12M hydrochloric acid and the mixture was refluxed for three hours. The solvent was subsequently removed under reduced pressure, the residue was taken up in dichloromethane, the solution was washed with saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. Removal of the solvent gave 1,8-dichloroanthracene as a yellow solid which was recrystallized from propanol.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 3 hours
  2. customthe solid was separated off via a Büchner funnel
  3. extractionThe aqueous phase was extracted three times with 150 ml each time of dichloromethane
  4. extractionthe solid was extracted a number of times with dichloromethane
  5. additionwhile being treated with ultrasound
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. customfreed of the solvent on a rotary evaporator
  8. temperature65 ml of 12M hydrochloric acid and the mixture was refluxed for three hours
  9. customThe solvent was subsequently removed under reduced pressure
  10. washthe solution was washed with saturated sodium hydrogen carbonate solution
  11. dry with materialdried over magnesium sulfate
  12. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-c1f03bc85f5641c488146610f299188a
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977312B2

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