3'-(Trifluoromethyl)acetophenone → Ethanone, 1-[3-(trifluoromethyl)phenyl]-, oxime

HRID 1648416Notes

Reaction equation

HRID 1648416 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:15][OH:16].O.O.O.C([O-])(=O)C.[Na+]>CO>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:9](=[N:15][OH:16])[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 676823'-(Trifluoromethyl)acetophenoneHCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 280810Ethanone, 1-[3-(trifluoromethyl)phenyl]-, oximeYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.5 g of 3'-trifluoromethylacetophenone, 6.25 g of hydroxylamine hydrochloride, and 8.8 g of sodium acetate trihydrate were heated in 125 ml of methanol under reflux for one hour. After completion of the reaction, the methanol was distilled off under reduced pressure. 190 ml of water was added to the resulting residue, followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and stripped of the solvent by distillation under reduced pressure to obtain 7.3 g of 3'-trifluoromethylacetophenone oxime having a melting point of 63° to 65° C.

Workup

  1. temperatureunder reflux for one hour
  2. customAfter completion of the reaction
  3. distillationthe methanol was distilled off under reduced pressure
  4. addition190 ml of water was added to the resulting residue
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  7. distillationstripped of the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-a6ae573a77f24af4bc7754f138876773
Source dataset
uspto-grants-1995_07
Patent number
US05436267

Reaction notes

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