Cou
National Hazard
Posts: 958
Registered: 16-5-2013
Member Is Offline
Mood: Mad Scientist
|
|
Fisher esterification of citric acid and acetic acid to make this?
http://www.chemicalize.org/structure/#!mol=2-%28acetyloxy%29...
O-acetylcitric acid
[Edited on 29-3-2015 by Cou]
|
|
|
Bert
|
Thread Moved
28-3-2015 at 19:29 |
Darkstar
Hazard to Others
Posts: 279
Registered: 23-11-2014
Member Is Offline
Mood: Sleepy
|
|
In theory it would work, but your yield is probably going to be extremely low at best. Since the hydroxyl group in citric acid is tertiary, the
competing elimination reaction is going to be the more favorable of the two. I would imagine the desired acetylation could be achieved in good yields
using acetyl chloride in Et3N, pyridine or some other similar base, preferably under anhydrous conditions. Knowing you, though, I'm pretty
sure you're not going to want to work with an acyl chloride.
Not that I blame you.
|
|
|
Chemosynthesis
International Hazard
Posts: 1071
Registered: 26-9-2013
Member Is Offline
Mood: No Mood
|
|
Agreed. I did the acetyl chloride esterification listed for an industrial production method of other esters of citric acid. I forget where.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
