Acetone Cyanohydrin → 2-[2-Chloro-4-(methylsulfonyl)benzoyl]-4,4-dimethyl-5-phenyl-1,3-cyclohexanedione

HRID 35504

Reaktionsgleichung

Reaktionsgleichung von HRID 35504
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:15][C:16]1([CH3:30])[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][C:19](=[O:28])[CH2:18][C:17]1=[O:29].C(N(CC)CC)C.CC(C)(O)C#N>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([CH:18]1[C:17](=[O:29])[C:16]([CH3:30])([CH3:15])[CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20][C:19]1=[O:28])=[O:5]

Komponenten

6

Edukt 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 110960194,4-Dimethyl-5-phenyl-1,3-cyclohexanedioneHCID 11128804Benzoyl chloride, 2-chloro-4-(methylsulfonyl)-

Produkt 1

HCID 142776582-[2-Chloro-4-(methylsulfonyl)benzoyl]-4,4-dimethyl-5-phenyl-1,3-cyclohexanedioneAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Chloro-4-(methylsulfonyl)benzoyl chloride (2.3 g, 9 mmol) and 4,4-dimethyl-5-phenyl-1,3-cyclohexanedione (2.0 g, 9 mmol) were dissolved in 50 ml of acetonitrile. Triethylamine (1.8 g, 18 mmol) was added dropwise and the resulting solution was stirred at room temperature for 1 hour. Acetone cyanohydrin (0.17 g, 2 mmol) and triethylamine (1.8 g, 18 mmol) were added and the reaction mixture was stirred at room temperature for 1.5 hour. The reaction mixture was concentrated under vacuum and the residue dissolved in 100 ml of methylene chloride. The methylene chloride solution was washed with 2N hydrochloric acid, 10% cupric acetate, water, 5% potassium carbonate, 2N hydrochloric acid, and water. The methylene chloride solution was dried over anhydrous magnesium sulate and concentrated under vacuum, yielding 1.2 g of the desired product as a viscous oil. It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 1.5 hour
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutionthe residue dissolved in 100 ml of methylene chloride
  4. washThe methylene chloride solution was washed with 2N hydrochloric acid, 10% cupric acetate, water, 5% potassium carbonate, 2N hydrochloric acid, and water
  5. dry with materialThe methylene chloride solution was dried over anhydrous magnesium sulate
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-51477c7e58d44a60921bf4f83a6b5d47
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767447

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