Salicylaldoxime

Salicylaldoxime is an organic compound described by the formula C6H4CH=NOH-2-OH and it is the oxime of salicylaldehyde. This crystalline, colorless solid is a chelator and sometimes used in the analysis of samples containing transition metal ions, with which it often forms brightly colored coordination complexes.

Salicylaldoxime is recognized as a selective precipitant for copper, although it forms water-insoluble chelates with a number of elements. Ingvar Dahl invested the extraction of divalent magnesium, manganese, cobalt, nickel, copper, zinc, cadmium, mercury, and lead with solutions of salicylaldoxime in benzene and the effect of the reagent concentration and particularly the pH of the aqueous phase on the extractability was also studied. The solubility of salicylaldoxime in organic solvents has been utilized in the solvent extraction of carious elements.

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The general procedure for the synthesis of salicylaldehyde oxime from salicylaldehyde is as follows: 30 mmol of 2-hydroxybenzaldehyde, 60 mmol of sodium bicarbonate, and 45 mmol of hydroxylamine hydrochloride were dissolved in a mixed ethanol/water solvent (50 mL of ethanol/5 mL of water) at room temperature. The reaction mixture was stirred for 2 hours, followed by removal of most of the solvent by concentration. The residue was diluted with ethyl acetate and filtered directly. The filtrate was concentrated to give a final 3.99 g (98% yield) of the colorless oily product salicylaldoxime.