Sodium Hydroxide → 2-(4-Chlorophenyl)cyclobutanone oxime

HRID 1482438Notes

Reaction equation

HRID 1482438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][CH2:10][C:9]2=O)=[CH:4][CH:3]=1.Cl.[NH2:14][OH:15].[OH-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][CH2:10][C:9]2=[N:14][OH:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 898230052-(4-Chlorophenyl)cyclobutanone

Product 1

HCID 1317367062-(4-Chlorophenyl)cyclobutanone oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-chlorophenyl)cyclobutanone (1.122 g, 6.09 mmol), hydroxylamine hydrochloride (3.541 g. 8.2 eq.) and 36 ml of 5% NaOH in 30 ml EtOH was heated at reflux for 2 h. The solution was cooled, adjusted to pH 6, and extracted with CHCl3. The organic extract was washed with brine and dried. Filtration and concentration yielded 2-(4-chlorophenyl)cyclobutanone oxime as an oil. 1 g (84%)

Workup

  1. temperatureat reflux for 2 h
  2. temperatureThe solution was cooled
  3. extractionextracted with CHCl3
  4. extractionThe organic extract
  5. washwas washed with brine
  6. customdried
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-5cb33c3b4ce54ca58200a6b306d41575
Source dataset
uspto-grants-2016_08
Patent number
US09414589B2

Reaction notes

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