Hydroxyamine hydrochloride → Methyl 3-hydroxyiminomethyl-4-methylsulfonyl-2-methylbenzoate

Participants

Reaction Steps

11.55 g of methyl 3-formyl-4-methylsulfonyl-2-methylbenzoate was dissolved in 100 ml of ethanol, and 4.70 g of hydroxylamine hydrochloride was added. The resulting solution was reacted for 1.5 hours at room temperature and further heated at reflux for an hour. The reaction solution was cooled down. Ethanol was then distilled out under reduced pressure. The obtained residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure to give 12.31 g of a crude product as viscous oil. The crude product was purified by column chromatography on silica gel with n-hexane/ethyl acetate=2/1 to give the title compound as white crystals. m.p. 123~129° C.

Provenance & Evidence