Hydroxylamine HCl → 2,2,2-Trifluoro-1-(2,4,6-trimethylphenyl)ethanone oxime

HRID 1636017Notes

Reaction equation

HRID 1636017 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13])=O.[Cl-].[OH:17][NH3+:18].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13])=[N:18][OH:17]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 5205212,2,2-Trifluoro-2',4',6'-trimethylacetophenone

Product 1

HCID 734559532,2,2-Trifluoro-1-(2,4,6-trimethylphenyl)ethanone oximeYield 28.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6.3 g (0.029 mol) of 2,2,2-trifluoro-1-(2,4,6-trimethylphenyl)-ethanone are dissolved in 30 ml of ethanol at 80° C. To the solution are added dropwise 2.0 g (0.029 mol) of hydroxylammonium chloride and 4.1 g (0.050 mol) of sodium acetate dissolved in 15 ml of water. The reaction mixture is refluxed overnight, poured into ice water, and extracted with ethyl acetate. The organic phase is washed with brine, dried over MgSO4, and concentrated. The residue is purified by recrystallization from 20 ml of hexane, yielding 1.9 g of 2,2,2-trifluoro-1-(2,4,6-trimethylphenyl)-ethanone oxime in the form of white crystals, mp. 119-125° C.

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by recrystallization from 20 ml of hexane

Sources & evidence

ORD record
ord-3d1bcb0f6e9d440c961294755b5906d5
Source dataset
uspto-grants-2003_01
Patent number
US06512020B1

Reaction notes

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