[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:17][OH:18].[OH-].[Na+]>CO>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=[N:17][OH:18])[CH3:12])[CH:6]=[CH:7][CH:8]=1In a 250 ml single neck flask was charged 6.4 g (29.9 mmoles, 1.0 eq.) of 4-(3-trifluoromethylphenyl)-3-buten-2-one and 5.2 g (75.4 mmoles, 2.5 eq) of hydroxylamine hydrochloride and 6 g of 50% sodium hydroxide (75 mmoles, 2.5 eq) and 100 ml of methanol. The reaction mixture was stirred at reflux for 2 hours. The reaction mixture was concentrated, diluted with water (50ml), and then extracted with ethyl acetate (2×50 ml). The organic phase was dried and concentrated, to obtain 4.4 g of 4-(3-trifluoromethylphenyl)-3-buten-2-one 2-oxime (E/Z mixture of isomers) as an oil in 64.2% yield.
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