Hydrochloric Acid → alpha,3-Dichlorobenzaldoxime

HRID 331814Notes

Reaction equation

HRID 331814 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)/[CH:5]=[N:6]\[OH:7].[ClH:11].OS([O-])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+]>CN(C=O)C>[OH:7]/[N:6]=[C:5](\[Cl:11])/[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5372364Benzaldehyde, m-chloro-, oxime, (Z)-HCID 15793144Potassium caroate

Product 1

HCID 10943262alpha,3-DichlorobenzaldoximeYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)- and/or (Z)-3-chloro-benzaldehyde oxime (54 g, 347 mmol) in DMF (800 mL) was added HCl (conc., 17 mL) and the mixture cooled to room temperature. Then potassium monopersulfate triple salt (247 g, 400 mmol) and the reaction mixture was stirred at room temperature for 1 h. The mixture was then poured onto ice-water, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated to afford the title compound (66 g, 100%) which was obtained as a white solid. Mp: 58-60° C.

Workup

  1. additionThe mixture was then poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-e8ea534cb75647e68d72a8985f5ac4ab
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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