Hydrochloric Acid → Ethyl 2-oxocyclohexanecarboxylate

HRID 512120Notes

Reaction equation

HRID 512120 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[H-].[Na+].[C:11]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl>C1COCC1.[Cl-].[Na+].O>[O:17]=[C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:1]([O:5][CH2:6][CH3:7])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 7967Cyclohexanone2×HCID 24758Sodium hydride

Product 1

HCID 95543Ethyl 2-oxocyclohexanecarboxylateYield 80.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A 1000 mL flashk was charged with diethyl carbonate (146 mL, 1.2 mol) and 150 mL of dry THF, and NaH (60%, 63 g, 1.6 mol) was added to the mixtrure under stirring. The mixture was heated to reflux for 1 h, and then, a solution of cyclohexanone (50 mL, 0.48 mol) in anhydrous THF (50 mL) was added dropwise to the mixture, and the addition of cyclohexanone was continued for ca. 0.5 h. The mixture was refluxed for an additional 1.5 h. After cooled, the mixture was hydrolyzed by 3N hydrochloric acid, then poured into brine, extracted by DCM (75 mL×3). The combined organic layer was dried and evaporated to give the title compound (66 g, 80% yield) as brown oil which was set to do next step without any purification. MS: m/z 171.3 [M+H]+.

Workup

  1. additionwas added to the mixtrure
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1 h
  4. temperatureThe mixture was refluxed for an additional 1.5 h
  5. temperatureAfter cooled
  6. extractionextracted by DCM (75 mL×3)
  7. customThe combined organic layer was dried
  8. customevaporated

Sources & evidence

ORD record
ord-98668d13fce34c5bb8f816cce0afaa57
Source dataset
uspto-grants-2015_08
Patent number
US09102631B2

Reaction notes

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