Hydroxylamine HCl → HCID 73455958, compound

HRID 1636016Notes

Reaction equation

HRID 1636016 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1C)=O.[Cl-].[OH:16][NH3+:17].[C:18]([O-])(=O)C.[Na+]>C(O)C.O>[F:14][C:2]([F:1])([F:13])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH3:18])=[CH:9][C:10]=1[CH3:11])=[N:17][OH:16]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 186745371-(2,6-Dimethylphenyl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 73455958HCID 73455958, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

12.6 g (0.062 mol) of 2,2,2-trifluoro-1-(2,6-dimethylphenyl)-ethanone are dissolved in 30 ml of ethanol at 80° C. To the solution are added dropwise 4.6 g (0.066 mol) of hydroxylammonium chloride and 8.7 g (0.106 mol) of sodium acetate dissolved in 15 ml of water. The reaction mixture is refluxed overnight, affording white precipitation. The mixture is poured into ice water, and extracted with ethyl acetate. The organic phase is washed with water, NH4Cl aq, and brine, dried over MgSO4, and concentrated, yielding 11.9 g of crude 2,2,2-trifluoro-1-(2,4-dimethylphenyl)-ethanone oxime as a colorless liquid. The crude product is used in the next reaction step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. customaffording white
  3. customprecipitation
  4. additionThe mixture is poured into ice water
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with water, NH4Cl aq, and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7c0bee1dc5584a8593ed51b729c955da
Source dataset
uspto-grants-2003_01
Patent number
US06512020B1

Reaction notes

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