Ethanol → (p-Chlorophenyl)-1,1,1-trifluoro-2-propanone oxime

HRID 484237Notes

Reaction equation

HRID 484237 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.C(O)C.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[N:19][OH:20])[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 151139833-(4-Chlorophenyl)-1,1,1-trifluoropropan-2-one

Product 1

HCID 85405208(p-Chlorophenyl)-1,1,1-trifluoro-2-propanone oximeYield 110.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 3-(p-Chlorophenyl)-1,1,1-trifluoro-2-propanone (10.0 g, 0.045 mol) and ethanol (60 mL) is treated with a solution of hydroxylamine hydrochloride (4.68 g, 0.067 mol) and water (20 mL) and then with a solution of sodium acetate (5.53 g, 0.067 mol) and water (20 mL). The reaction mixture is then refluxed for 2 hours, cooled to room temperature, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a liquid which solidifies upon standing to give the title product as white needles (11.84 g). Identified by IR and NMR spectral analyses.

Workup

  1. temperatureThe reaction mixture is then refluxed for 2 hours
  2. extractionextracted with ether
  3. washThe combined organic extracts are washed sequentially with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a liquid which

Sources & evidence

ORD record
ord-b262fd9b53444af0a49d60b931edfa21
Source dataset
uspto-grants-1993_07
Patent number
US05229524

Reaction notes

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