[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[CH3:11][CH:12]([CH3:19])[C:13](=O)[C:14](=[N:16][OH:17])[CH3:15].Cl.C(=O)([O-])O.[Na+]>C(O)(=O)C.COCCOC.COC(C)(C)C.O>[CH:12]([C:13]1[O:7][C:6]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=2)=[N+:16]([O-:17])[C:14]=1[CH3:15])([CH3:19])[CH3:11]19.0 g (137 mmol) of 3-methoxybenzaldehyde were added to a solution of 18.0 g (137 mmol) of 4-methylpentane-2,3-dione 2-oxime in 30 g (99 mmol) of solution of hydrogen chloride in acetic acid (12%) and 30 g (164 mmol) of solution of hydrogen chloride in ethylene glycol dimethyl ether (20%). The reaction was stirred at 50-55° C. for 3 hours and at room temperature for 60 hours. Subsequently, 500 ml of water and 300 ml of tert-butyl methyl ether were added before a pH of 3-4 was established by adding sodium hydrogen carbonate. After phase separation, the aqueous phase was extracted twice with 100 ml each time of tert-butyl methyl ether. The combined organic phases were washed with 4×100 ml of water and concentrated fully under reduced pressure.
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