Hydrochloric Acid → HCID 68732214, Verbindung

HRID 341675

Reaktionsgleichung

Reaktionsgleichung von HRID 341675
[CH3:1][C:2]1([CH3:13])[C:7](=[O:8])[C:6]([CH3:10])([CH3:9])[C:5](=[O:11])[CH2:4][C:3]1=[O:12].[CH:14](Cl)(Cl)Cl.[CH3:18][C:19]([CH2:21][C:22]([CH2:24][C:25](O)=O)=O)=O.Cl.[C:29]1([CH3:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C1C=CN=CC=1>[CH3:35][C:29]1[CH:34]=[C:33]([C:18]2[CH:25]=[CH:24][CH:22]=[CH:21][CH:19]=2)[CH:32]=[C:31]([CH3:14])[C:30]=1[CH:4]1[C:3](=[O:12])[C:2]([CH3:13])([CH3:1])[C:7](=[O:8])[C:6]([CH3:9])([CH3:10])[C:5]1=[O:11]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6212ChloroformHCID 54598443,5-Dioxohexanoic acidHCID 117691662,2,4,4-Tetramethylcyclohexane-1,3,5-trione

Produkt 1

HCID 68732214HCID 68732214, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

To a mixture of 2,2,4,4-tetramethylcyclohexane-1,3,5-trione (182 mg, 1 mmol) and 4-dimethylaminopyridine (610 mg, 5 mmol) under an atmosphere of nitrogen, is added dry chloroform (5.6 ml), followed by stirring at room temperature until dissolution is complete. To this solution is then added dry toluene (2 ml), and 3,5-dimethylbiphenylead triacetate (0.5 M solution in dry chloroform, 2.4 ml, 1.2 mmol). This solution is then heated under reflux for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH 1 with 2N aqueous hydrochloric acid, filtered and the filtrate is extracted with dichloromethane (2×40 ml). The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is further purified by column chromatography on silica gel to give 6-(3,5-dimethylbiphenyl-4-yl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione (166 mg).

Aufarbeitung

  1. temperatureThis solution is then heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered
  5. extractionthe filtrate is extracted with dichloromethane (2×40 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe residue is further purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-bca18a6890a54f3aab0a2c733f23c31a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895761B2

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