Cl[O-].[Na+].[Cl:4][C:5]1[C:14]([CH:15]=[CH2:16])=[C:13]([Cl:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:18][C:19]([CH3:24])([CH3:23])[CH:20]=[N:21][OH:22].Cl[O-]>ClCCl.O>[Cl:4][C:5]1[C:14]([CH:15]2[O:22][N:21]=[C:20]([C:19]([CH3:24])([CH3:23])[CH3:18])[CH2:16]2)=[C:13]([Cl:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]
17 ml of a 12% strength aqueous sodium hypochlorite solution were added dropwise at room temperature into a vigorously stirred solution of 2.6 g (10 mmol) of methyl 2,4-dichloro-3-ethenylbenzoate and 1 g (10 mmol) of 2,2-dimethylpropional-doxime in 100 ml of dichloromethane. After the mixture had been stirred for in each case 2 hours, two further portions of 0.5 g (5 mmol) of the oxime and 9 ml of the hypochlorite solution were added. Stirring was continued for 12 hours at room temperature, and the reaction mixture was then stirred into 350 ml of water. After extraction with dichloromethane, drying and removal of the solvent, the residue was chromatographed.
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