2-Ethylcyclohexanone → 2-Ethyl-1-(hydroxyimino)cyclohexane

HRID 890364

Reaction equation

HRID 890364 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O)[CH3:2].C([O-])(=O)C.[Na+].Cl.[NH2:16][OH:17]>O.C(O)C>[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[N:16][OH:17])[CH3:2]

Participants

6

Reactant 3

HCID 204742-EthylcyclohexanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 5746222-Ethyl-1-(hydroxyimino)cyclohexaneYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-ethylcyclohexanone (104.3 mmol) in water and ethanol, and sodium acetate (125.1 mmol) were added hydroxylamine hydrochloride (156.4 mmol), the reaction was heated at 70° C. overnight. The ethanol was removed under reduced pressure, and the reaction mixture was dissolved in water. The aqueous layer was extracted with ether, and the combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated to give 2-ethyl-1-(hydroxyimino)cyclohexane (52%) as a thick oil.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. dissolutionthe reaction mixture was dissolved in water
  3. extractionThe aqueous layer was extracted with ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-36d1fda336bd4efbb943c938ef9c8884
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Linked notes

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