Sodium Carbonate → 3,3-Dimethylcyclohexanone oxime

HRID 547668Notes

Reaction equation

HRID 547668 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=O)[CH2:3]1.Cl.[NH2:11][OH:12].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=[N:11][OH:12])[CH2:3]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 76322Cyclohexanone, 3,3-dimethyl-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 594582653,3-Dimethylcyclohexanone oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 3,3-dimethylcyclohexanone (4.0 g, 0.032 mol) and hydroxylamine hydrochloride (2.9 g, 0.041 mol) in ethanol (20 mL) was added dropwise a solution of sodium carbonate (4.3 g, 0.041 mol) in water (25 mL). The mixture was heated at reflux for 3 hours. The mixture was concentrated in vacuo to remove the ethanol and the aqueous residue was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated in vacuo to give 3,3-dimethylcyclohexanone oxime as a yellow oil. This material was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove the ethanol
  5. extractionthe aqueous residue was extracted with ethyl acetate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc52a2beb3c9464f9acefb0640c1fcc3
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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