Sciencemadness Discussion Board

O-Toluidine from N-Acetyl-Toluidine

liftedresearch - 18-11-2015 at 16:49

Hello all,

This is my first post here at Science Madness, but I have been using this site as a resource you have generously provided. Anyway, my question is how would one go about deacylating N-Acetyl-O-Toluidine back to O-Toluidine? I have used the search engine with no luck, I have also checked Google Scholar and got the same outcome. Thank you in advance.

AvBaeyer - 18-11-2015 at 18:40

Simple hydrolysis in 6N hydrochloric acid at reflux. Work up in the "usual manner" referring to the typical isolation of aniline type compounds from acidic solutions. There are several references/recipes which can be found in the forum library. Look up the hydrolysis of acetanilide to aniline.

AvB

liftedresearch - 19-11-2015 at 17:04

Thank you so much dor the quick response, i tried it, and from what i can tell it seems to be working. There is an evolution of acetic acid, Im assuming the reaction is done when the evolution of AcOH ceases, or is there something else to look for? Anyway, thanks again.