2-Methoxycyclohexanone → 1-(Hydroxyimino)-2-methoxycyclohexane

HRID 988967Notes

Reaction equation

HRID 988967 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.Cl.[NH2:11][OH:12].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:12][N:11]=[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 1109982-MethoxycyclohexanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 737992461-(Hydroxyimino)-2-methoxycyclohexane

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-methoxycyclohexanone (39.0 mmol), hydroxylamine hydrochloride (72 mmol), and sodium acetate (48.8 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)-2-methoxycyclohexane.

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-ff1f9e8e9cc043078702f2cf7756e6aa
Source dataset
uspto-grants-2003_10
Patent number
US06638927B2

Reaction notes

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