Keras - 15-11-2024 at 06:12
I read about the potential use of zinc dust in acetic acid as an acetylating mixture for amines/anilines. Does anyone know about this?
Also, it seems ethyl acetate + acetic acid works well as an acetylating mixture for amines and even anilines, given you’re prepared to reflux the
mixture at 90/110 °C for 20 hours or so. Yet, this process sidesteps the use of the hard to source/make acetic anhydride.
Dr.Bob - 15-11-2024 at 07:42
If you heat the mixture to over 100 C, then driving water off will certainly help promote the reaction. However, ethyl acetate's BP is about 78 C,
so that would not work out well.
Just putting an amine in acetic acid and heating would likely promote some amount of amide formation, and some metals or catalysts would likely help
that. Much like DMAP helps acetylate alcohols. Some amides can be formed by simply helping the acid and amine together, such as in Nylon 6
synthesis.
Keras - 15-11-2024 at 11:02
On the other hand, ethyl acetate and water are not miscible…
bnull - 15-11-2024 at 11:25
What about this: Green Acetylation of Primary Aromatic Amines (https://www.ias.ac.in/public/Volumes/reso/028/02/0325-0331.p...).
Keras - 15-11-2024 at 12:29
Nice paper. I’ll try to make paracetamol using this method the next weekend. I don’t have tartaric acid, but magnesium sulphate, oxalic and citric
acid, I do.