4-Phenylcyclohexanone → 4-Phenylcyclohexanone oxime

HRID 890370

Reaction equation

HRID 890370 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:16][N:15]=[C:10]1[CH2:11][CH2:12][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 786054-PhenylcyclohexanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 3438824-Phenylcyclohexanone oximeYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-phenylcyclohexanone (28.7 mmol), hydroxylamine hydrochloride (36.0 mmol), and sodium acetate (60.95 mmol) in ethanol and water was heated at 70° C. overnight. Ethanol was removed, and the residue was dissolved in water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated to give 1-(hydroxyimino)-4-phenylcyclohexane (97%).

Workup

  1. customEthanol was removed
  2. dissolutionthe residue was dissolved in water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d1c6e62fd48849e89adc22db2d64dcf8
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Linked notes

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