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

HRID 2372418Notes

Reaction equation

HRID 2372418 reaction equation
[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]

Participants

8

Reactant 5

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

Product 2

HCID 224023diethyl 2-oxocyclohexane-1,1-dicarboxylateYield 109.6%HCID 178418443HCID 178418443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.)

Workup

  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

Sources & evidence

ORD record
ord-da38a8d5c55a422ca760e581e75494a0
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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