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Acetonitrile → 2-((1R,4r)-4-(4-chlorophenyl)cyclohexyl)naphthalene-1,4-dione

HRID 2261877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2261877
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14](O)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(#N)C.[C:20]1(=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])[CH:22]=C1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([C:14]3[C:20](=[O:31])[C:29]4[C:24]([C:23](=[O:30])[CH:22]=3)=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1
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Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 85301,4-NaphthoquinoneHCID 62648Ammonium PersulfateHCID 178525693HCID 178525693, Verbindung

Produkt 1

HCID 251644132-((1R,4r)-4-(4-chlorophenyl)cyclohexyl)naphthalene-1,4-dioneAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470
Silver Nitrate
Katalysator
HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
31 °C

Versuchsvorschrift

To a solution of silver nitrate (14.17 g, 0.0838 moles) dissolved in 200 ml water, 100 gm (0.419 moles) trans-4-(4-chlorophenyl)cyclohexane carboxylic acid and acetonitrile (500 ml) was added. The solution was heated to reflux followed by addition of 1,4-naphthoquinone (80 gm, 0.506 moles). A solution of ammonium persulfate (239 g; 1.048 moles) in water (600 ml) was added dropwise to the above solution and continued reflux for half an hour. The reaction mass was then cooled to 30-32° C. and extracted with methylene chloride. The organic layer was first washed with water, followed with 10% sodium carbonate aqueous solution, and further with water until neutral pH. The organic layer was concentrated to afford the compound of Formula II (2-[4-(4-chlorophenyl)cyclohexyl]-1,4-naphthoquinone, 149 gm).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperaturecontinued reflux for half an hour
  4. extractionextracted with methylene chloride
  5. washThe organic layer was first washed with water
  6. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d66767c3ca15487388ba6d100ffe5c4c
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07847127B2

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