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Acetone Cyanohydrin → 2-(4-Methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dione

HRID 36561
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 36561
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:24][C:25]1([CH3:33])[CH2:30][C:29](=[O:31])[CH2:28][C:27](=[O:32])[CH2:26]1.CC(C)(O)C#N>ClCCl>[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([CH:28]2[C:29](=[O:31])[CH2:30][C:25]([CH3:33])([CH3:24])[CH2:26][C:27]2=[O:32])=[O:10])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)(=[O:4])=[O:3]
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Komponenten

6

Edukt 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 31358DimedoneHCID 148001864-(Methanesulfonyl)-2-nitrobenzoyl chloride

Produkt 1

HCID 199371392-(4-Methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dioneAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-methylsulphonyl-2-nitrobenzoyl chloride (9.62 g) in dry dichloromethane (50 ml) was added to a stirred solution of triethylamine (5.6 ml) and 5,5-dimethylcyclohexane-1,3-dione (5 g) in dry dichloromethane (70 ml) during 30 minutes and the reaction mixture stirred at ambient temperature for 4 hours. Triethylamine (15.3 ml) and acetone cyanohydrin (0.5 ml) were added successively and the reaction mixture stirred at ambient temperature for 18 hours. The reaction mixture was washed successively with 2N hydrochloric acid (2×50 ml) and water (2×50 ml), dried over magnesium sulphate and evaporated under reduced pressure to give a yellow glass which was recrystallised from methanol (20 ml) to give 2-(4-methylsulphonyl-2-nitrobenzoyl)-5,5-dimethylcyclohexane-1,3-dione (6.4 g), m.p. 156.5°-158° C., as a yellow crystalline solid.

Aufarbeitung

  1. stirringthe reaction mixture stirred at ambient temperature for 18 hours
  2. washThe reaction mixture was washed successively with 2N hydrochloric acid (2×50 ml) and water (2×50 ml)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a yellow glass which
  6. customwas recrystallised from methanol (20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-d58fcbdd740644d9af498b7e9b6eb406
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05416061

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