Hydrochloric Acid → Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate

HRID 1750736Notes

Reaction equation

HRID 1750736 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1.[CH3:12][O:13][C:14](=O)[O:15]C.Cl>O1CCCC1.CCCCCC>[CH3:3][C:4]1([CH3:11])[CH2:9][CH:8]([C:14]([O:13][CH3:12])=[O:15])[C:7](=[O:10])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 138166Cyclohexanone, 4,4-dimethyl-

Product 1

HCID 12441545Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension of hexane-washed NaH (0.72 g, 60%, 18 mmol) in tetrahydrofuran (30 mL) was added a solution of 4,4-dimethylcyclohexanone (2.0 g, 15.6 mmol) in tetrahydrofuran (20 mL). The suspension was stirred at room temperature for 30 minutes. Then dimethylcarbonate (6.31 mL, 75 mmol) was added dropwise by syringe. The mixture was heated to reflux for four hours. The mixture was acidified with 5% HCl and extracted with dichloromethane (100 mL×3) and washed with water, brine, and dried over Na2SO4. After concentration, the crude product was loaded on a column and eluted with 10% ethyl acetate in hexane to give title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for four hours
  3. extractionextracted with dichloromethane (100 mL×3)
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ea09579c02d14500aa579a58bd62f783
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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