Sulfuric Acid → 2-(4-Propyl-cyclohexanecarbonyl)-malonic acid diethyl ester

HRID 1725181

Reaktionsgleichung

Reaktionsgleichung von HRID 1725181
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:13]([CH:16]1[CH2:21][CH2:20][CH:19]([C:22](Cl)=[O:23])[CH2:18][CH2:17]1)[CH2:14][CH3:15].OS(O)(=O)=O>CCO.C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(Cl)(Cl)(Cl)Cl>[CH2:11]([O:10][C:2](=[O:9])[CH:3]([C:22]([CH:19]1[CH2:20][CH2:21][CH:16]([CH2:13][CH2:14][CH3:15])[CH2:17][CH2:18]1)=[O:23])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

Komponenten

9

Edukt 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224Magnesium2×HCID 12780024Cyclohexanecarbonyl chloride, 4-propyl-, trans-

Produkt 1

HCID 690599802-(4-Propyl-cyclohexanecarbonyl)-malonic acid diethyl esterAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To 2.5 mL of anhydrous EtOH and 0.25 mL carbon tetrachloride was added 1.2 g (50 mmol) magnesium turnings. 8.0 g (50 mmol) diethyl malonate was dissolved in a mixture of 5 mL anhydrous EtOH and 20 mL anhydrous toluene and added in small portions to the magnesium turnings over the course of 1.5 hr so as to maintain a gentle reflux. The reaction was stirred at room temperature for 1 hr, and then cooled to 0° C. in ice. 4-Propyl-cyclohexanecarbonyl chloride (50 mmol) was added dropwise and the reaction was allowed to warm to room temperature over night. The reaction was then heated to 55° C. for 4 hr with stirring, allowed to cool to ambient temperature, and was poured into a slurry of crushed ice and 10% H2SO4. The solution was diluted with brine and extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated to afford 10.71 g (34.28 mmol) 2-(4-propyl-cyclohexanecarbonyl)-malonic acid diethyl ester as a clear, near colorless oil.

Aufarbeitung

  1. temperatureto maintain a gentle reflux
  2. temperaturecooled to 0° C. in ice
  3. temperatureto warm to room temperature over night
  4. temperatureThe reaction was then heated to 55° C. for 4 hr
  5. stirringwith stirring
  6. temperatureto cool to ambient temperature
  7. extractionextracted with ethyl acetate
  8. customThe organic layer was separated
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-44c439965f4b4537b0c76da3e33c7e09
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488832B2

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