Hydrochloric Acid → alpha,3-Dichlorobenzaldoxime

HRID 1911641Notes

Reaction equation

HRID 1911641 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-bb20aeb039ec46e499d36c2a7889852e
Source dataset
uspto-grants-2013_12
Patent number
US08604062B2

Reaction notes

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