Sulfuric Acid → Diethyl 2-oxocyclohexane-1,1-dicarboxylate

HRID 2372418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2372418
[Br:1]CC.[Mg:4].[C:5]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16])([O:7][CH2:8][CH3:9])=[O:6].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].S(=O)(=O)(O)O>O1CCCC1>[CH2:15]([Mg:4][Br:1])[CH3:10].[C:5]([C:10]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16])([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 6332Ethyl BromideHCID 10928Ethyl chloroformateHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 5462224Magnesium

Produkt 2

HCID 224023Diethyl 2-oxocyclohexane-1,1-dicarboxylateAusbeute 109,6 %HCID 178418443HCID 178418443, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A tetrahydrofuran solution (30 ml) of ethylmagnesium bromide was prepared from bromoethane (7.05 g.) and magnesium (1.5 g.) The solution was cooled to 0° and 2-carbethoxycyclohexanone (10.0 g.) was added carefully. The reaction mixture was stirred at room temperature for 30 minutes and ethyl chloroformate (7.0 g.) was added dropwise, under nitrogen. A white precipitate developed. Sulphuric acid solution (80 ml, 1%) was added and the aqueous mixture was extracted with ether. The ether extracts were washed with dilute aqueous sodium hydrogen carbonate solution, water and then dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. Distillation gave 2,2-dicarbethoxy-cyclohexanone (7.8 g.), a colourless oil, (b.pt. 98°-102° 0.9 mm.)

Aufarbeitung

  1. temperaturewas cooled to 0°
  2. extractionthe aqueous mixture was extracted with ether
  3. washThe ether extracts were washed with dilute aqueous sodium hydrogen carbonate solution, water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. distillationDistillation

Quellen und Nachweise

ORD-Eintrag
ord-da38a8d5c55a422ca760e581e75494a0
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05098929

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