4-Hydroxybenzaldehyde → 4-Hydroxybenzaldehyde oxime

Participants

Reaction Steps

Into a 500 ml round bottom flask equipped with a magnetic stirring bar, 40.49 g (331.6 mmol) of 4-hydroxybenzaldehyde were added. The aldehyde was dissolved in 240 ml methanol. To the stirred solution, 22.99 g (348.1 mmol) of 50% aqueous solution of hydroxylamine was added over a 15 min. period. The mixture was stirred for an additional 2 hr, at which time it was judged to be complete by the disappearance of the starting aldehyde as observed by thin layer chromatography (SiO2/CH3OH: CH2CL2 5:95). The solvent was removed in vacuo to give the product 4-hydroxybenzaldehyde oxime as a dark tan oil, which was recrystallized from water.

Provenance & Evidence