Hydrochloric Acid → 6-Undecanone oxime

HRID 1033469Notes

Reaction equation

HRID 1033469 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl.[NH2:14][OH:15].[OH-].[K+].Cl>C(O)C.O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[N:14][OH:15])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 135616-UndecanoneHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 5519936-Undecanone oximeYield 100.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

To a solution of 5.11 g of 6-undecanone in 20 ml of ethanol were successively added a solution of 3.47 g of hydroxylamine hydrochloride in 6 ml of water and a solution of 4.77 g of potassium hydroxide in 6 ml of water. The resulting mixture was heated under reflux for 3 hours. The reaction mixture was then poured into 150 ml of ice-containing water. The resulting aqueous mixture was made acidic by addition of 2N hydrochloric acid, and extracted with benzene. The organic layer was washed with saturated aqueous sodium chloride and evaporated under reduced pressure to remove the solvent. There was obtained 5.57 g (corresponding to theoretical amount) of 6-undecanone oxime as a pale yellow solid,

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with benzene
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customevaporated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-273b1fa09bfb4677a6a748102e5cfcd3
Source dataset
uspto-grants-1994_05
Patent number
US05310902

Reaction notes

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