Sodium Carbonate → N-(4,4-dimethylcyclohexylidene)hydroxylamine

HRID 547656

Reaction equation

HRID 547656 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][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][C:5](=[N:11][OH:12])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 279448N-(4,4-dimethylcyclohexylidene)hydroxylamineYield 88.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4,4-dimethylcyclohexanone (3.0 g, 0.024 mole) and hydroxylamine hydrochloride (2.2 g, 0.031 mole) in a mixture of ethanol (15 mL) and water (20 mL) at room temperature was added dropwise a solution of sodium carbonate (3.3 g, 0.031 mole) in water (10 mL). The mixture was heated at reflux for 3 hours, cooled to room temperature and concentrated in vacuo to remove the ethanol. The aqueous residue was extracted several times with ethyl acetate. The organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give 3.0 g (88%) of the desired 4,4-dimethylcyclohexanone oxime as a white solid. This was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-aca40312be384b04bd2088198325918f
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Linked notes

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