Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Acetylation of amides/anilines with zinc and acetic acid
Keras
National Hazard
****




Posts: 945
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline


[*] posted on 15-11-2024 at 06:12
Acetylation of amides/anilines with zinc and acetic acid


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.
View user's profile View All Posts By User
Dr.Bob
International Hazard
*****




Posts: 2759
Registered: 26-1-2011
Location: USA - NC
Member Is Offline

Mood: Mildly disgruntled scientist

[*] posted on 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.
View user's profile View All Posts By User
Keras
National Hazard
****




Posts: 945
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline


[*] posted on 15-11-2024 at 11:02


On the other hand, ethyl acetate and water are not miscible…
View user's profile View All Posts By User
bnull
Hazard to Others
***




Posts: 486
Registered: 15-1-2024
Location: South of the border, wherever the border is.
Member Is Offline

Mood: Happy New Year!

[*] posted on 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...).



Quod scripsi, scripsi.

B. N. Ull

P.S.: Did you know that we have a Library?
View user's profile View All Posts By User
Keras
National Hazard
****




Posts: 945
Registered: 20-8-2018
Location: (48, 2)
Member Is Offline


[*] posted on 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.

View user's profile View All Posts By User

  Go To Top