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

HRID 852628Notes

Reaction equation

HRID 852628 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH2:10][OH:11].Cl.C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[N:10][OH:11])[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 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4,4-dimethylcyclohexanone (D294) (9.2 g, 73 mmol, 1 equiv) in EtOH (50 ml) and H2O (50 ml) were added NH2OH.HCl (6.6 g, 94.5 mmol, 1.3 equiv) and Na2CO3 (10.06 g, 94.5 mmol, 1.3 equiv) and the resulting cloudy solution was refluxed for 2 h then cooled to room temperature. Most of EtOH was removed in vacuo and the aqueous phase was extracted twice with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give 4,4-dimethylcyclohexanone oxime (D296) (10 g, 97%) as a colourless solid which was used in the next step without purification.

Workup

  1. temperaturethe resulting cloudy solution was refluxed for 2 h
  2. customMost of EtOH was removed in vacuo
  3. extractionthe aqueous phase was extracted twice with AcOEt
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51accac78f5a430abb4c4e24a7f8d3f0
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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