Hydroxylamine HCl → N-[2,2,2-Trifluoro-1-(2-methylphenyl)ethylidene]hydroxylamine

HRID 1636015Notes

Reaction equation

HRID 1636015 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=O.[Cl-].[OH:15][NH3+:16].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=[N:16][OH:15]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 132386472,2,2-Trifluoro-1-(2-methylphenyl)ethan-1-one

Product 1

HCID 71329090N-[2,2,2-Trifluoro-1-(2-methylphenyl)ethylidene]hydroxylamineYield 66.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3.7 g (0.020 mol) of 2,2,2-trifluoro-1-(2-methylphenyl)-ethanone are dissolved in 20 ml of ethanol at 80° C. To the solution are added dropwise 1.4 g (0.020 mol) of hydroxylammonium chloride and 2.7 g (0.033 mol) of sodium acetate dissolved in 10 ml of water. The reaction mixture is refluxed for 5 hours, poured into ice water, and extracted with ethyl acetate. The organic phase is washed with water and brine, dried over MgSO4, and concentrated, yielding 2.7 g of 2,2,2-trifluoro-1-(2-methylphenyl)-ethanone oxime as a white solid. The crude product is used in the next reaction step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc9e921166f84df498f56db3a520fac5
Source dataset
uspto-grants-2003_01
Patent number
US06512020B1

Reaction notes

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