Dimethyl Carbonate → 3-Methyl-2-oxo-3-phenyl-cyclohexanecarboxylic acid methyl ester

HRID 1354094Notes

Reaction equation

HRID 1354094 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[H-].[Na+].[C:17](=O)([O:20]C)[O:18][CH3:19]>C1C=CC=CC=1>[CH3:19][O:18][C:17]([CH:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:1])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]1=[O:8])=[O:20]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 3499432-Methyl-2-phenylcyclohexanone

Product 1

HCID 588660533-Methyl-2-oxo-3-phenyl-cyclohexanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-methyl-2-phenylcyclohexanone (4.7 g, 25 mmol) from Preparation 3 above, and sodium hydride (1.1 g of 60% dispersion in mineral oil, 28 mmol) in 15 mL of dimethyl carbonate and 75 mL of benzene, was heated under reflux for 4 h. The mixture was cooled to room temperature and poured into dilute ice-cold aqueous HCl. The organic layer was washed with brine, dried (sodium sulfate) and evaporated to afford 6.36 g of 3-methyl-2-oxo-3-phenyl-cyclohexanecarboxylic acid methyl ester as an oil.

Workup

  1. customfrom Preparation 3 above
  2. temperatureunder reflux for 4 h
  3. additionpoured into dilute ice-cold aqueous HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-540dd7ad4c25407cbdb9e4569a629862
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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