Dimethyl Carbonate → METHYL 4,4-DIMETHYL-2-OXOCYCLOHEXANECARBOXYLATE

HRID 1619392Notes

Reaction equation

HRID 1619392 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1.[H-].[Na+].[C:12](=O)([O:15]C)[O:13][CH3:14]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([C:12]([O:13][CH3:14])=[O:15])[C:4](=[O:8])[CH2:3]1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 76322Cyclohexanone, 3,3-dimethyl-

Product 1

HCID 5314361METHYL 4,4-DIMETHYL-2-OXOCYCLOHEXANECARBOXYLATE

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3,3-dimethylcyclohexanone (0.5 g, 3.97 mmol, 1 equiv) and sodium hydride in toluene was stirred at rt for half an hour. To the mixture was added dimethyl carbonate and heated at reflux for 5 h. After the reaction was cooled to rt, the reaction mixture was quenched with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure to give the crude product, which was directly used for the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. customthe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d546ada348d4a088d8cbc1313ab3dab
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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