Chloro-oxime Dimerization

Reacted oxime to chloro-oxime - formed product, but impurity formed upon leaving the flask out at room temperature overnight. The product turned from yellow to red.

TCL analysis (1:1 Hexanes:DCM) determined that there was an impurity at baseline. The chloro-oxime was stable enough to remove said impurity by column chromatography to obtain the pure product.