Acetone Cyanohydrin → 2-(2-Chloro-4-methylsulfonyloxybenzoyl)-5-methyl-cyclohexane-1,3-dione

HRID 1534314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534314
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.C(N(CC)CC)C.[Cl:17][C:18]1[CH:26]=[C:25]([O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].S(Cl)(Cl)=O.CC(C)(O)C#N>C(Cl)Cl.C(#N)C>[Cl:17][C:18]1[CH:26]=[C:25]([O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:23][C:19]=1[C:20]([CH:5]1[C:6](=[O:8])[CH2:7][CH:2]([CH3:1])[CH2:3][C:4]1=[O:9])=[O:21]

Komponenten

8

Edukt 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 24386Thionyl ChlorideHCID 4580955-Methylcyclohexane-1,3-dioneHCID 18979827HCID 18979827, Verbindung

Produkt 1

HCID 150293212-(2-Chloro-4-methylsulfonyloxybenzoyl)-5-methyl-cyclohexane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of 5-methylcyclohexane-1,3-dione (1.79 g, 14.0 mmol) in 20 ml of methylene chloride containing triethylamine (2.90 ml, 20.8 mmol) is added, dropwise at 0°, a solution of 2-chloro-4-methylsulfonyloxybenzoyl chloride, prepared from the corresponding acid (3.50 g, 14.0 mmol) and thionyl chloride, in methylene chloride (10 ml). After the addition is complete, the mixture is stirred for another 30 min. at 0°, after which it is diluted with methylene chloride, washed, dried and evaporated to dryness. The crude enol ester is treated with triethylamine (3.97 ml, 2 eq.) and acetone cyanohydrin (0.4 ml) in 25 ml of acetonitrile. After stirring overnight at RT, the reaction mixture is concentrated and poured into water. The combined organic extracts are washed with dilute HCl and with brine, dried and evaporated to dryness. The crude product is crystallized from ether to give 2-(2-chloro-4-methylsulfonyloxybenzoyl)-5-methyl-cyclohexane-1,3-dione.

Aufarbeitung

  1. additionis added, dropwise at 0°
  2. additionAfter the addition
  3. washwashed
  4. customdried
  5. customevaporated to dryness
  6. stirringAfter stirring overnight at RT
  7. concentrationthe reaction mixture is concentrated
  8. additionpoured into water
  9. washThe combined organic extracts are washed with dilute HCl and with brine
  10. customdried
  11. customevaporated to dryness
  12. customThe crude product is crystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-e80e0e4d013040c8b63dd3b225269bc6
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089046

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