Potassium Carbonate → Methyl 2,4-dichloro-(2-hydroxyiminobut-3-en-4-yl)benzoate

HRID 1276136Notes

Reaction equation

HRID 1276136 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].[Cl:10][C:11]1[C:20]([CH:21]=[CH:22][C:23](=O)[CH3:24])=[C:19]([Cl:26])[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]>C(O)C.O>[Cl:10][C:11]1[C:20]([CH:21]=[CH:22][C:23](=[N:2][OH:3])[CH3:24])=[C:19]([Cl:26])[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 54401157Methyl 2,4-dichloro-3-(2-oxobut-3-en-4-yl)benzoate

Product 1

HCID 73865896Methyl 2,4-dichloro-(2-hydroxyiminobut-3-en-4-yl)benzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1.8 g (25.9 mmol) of hydroxylamine hydrochloride and 1.5 g (11.0 mmol) of potassium carbonate were added to 5.0 g (18.3 mmol) of methyl 2,4-dichloro-3-(2-oxobut-3-en-4-yl)benzoate in 160 ml of ethanol, and the reaction mixture was admixed with water until a clear solution was obtained. The mixture was heated under reflux for 3 hours and then cooled and the reaction mixture was taken up in 400 ml of water and extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed. Methyl 2,4-dichloro-(2-hydroxyiminobut-3-en-4-yl)benzoate was obtained in quantitative yield.

Workup

  1. customwas obtained
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. customThe combined organic phases were dried
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-297ec87aa4804718b9836e080ac79357
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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