Hunterman2244
Hazard to Others
Posts: 105
Registered: 6-6-2018
Member Is Offline
|
|
Aspirin to phenyl acetate
Is the any way to convert ASA to phenyl acetate?
|
|
|
CuReUS
National Hazard
Posts: 928
Registered: 9-9-2014
Member Is Offline
Mood: No Mood
|
|
http://pubs.rsc.org/en/content/articlelanding/2012/cc/c2cc33...
|
|
|
Hunterman2244
Hazard to Others
Posts: 105
Registered: 6-6-2018
Member Is Offline
|
|
I don't have access to that article.
Edit: found the given pdf, not too good of a yield, and expensive reagents
[Edited on 9-8-2018 by Hunterman2244]
|
|
|
Tsjerk
International Hazard
Posts: 3022
Registered: 20-4-2005
Location: Netherlands
Member Is Offline
Mood: Mood
|
|
Sci-hub.tw
|
|
|
Hunterman2244
Hazard to Others
Posts: 105
Registered: 6-6-2018
Member Is Offline
|
|
Thanks!
|
|
|
clearly_not_atara
International Hazard
Posts: 2692
Registered: 3-11-2013
Member Is Offline
Mood: Big
|
|
I'd guess you could get some kind of result by refluxing it in acetonitrile with CuI and maybe pyridine.
[Edited on 04-20-1969 by clearly_not_atara]
|
|
|
Hunterman2244
Hazard to Others
Posts: 105
Registered: 6-6-2018
Member Is Offline
|
|
Could it be done by decarboxylation?
|
|
|
clearly_not_atara
International Hazard
Posts: 2692
Registered: 3-11-2013
Member Is Offline
Mood: Big
|
|
wat
I'd be very surprised if it could be done any other way! It's a formal decarboxylation! What kind of question is this?
[Edited on 04-20-1969 by clearly_not_atara]
|
|
|
Hunterman2244
Hazard to Others
Posts: 105
Registered: 6-6-2018
Member Is Offline
|
|
I meant decomposition. Like heatwise
|
|
|
ELRIC
Hazard to Others
Posts: 244
Registered: 23-2-2015
Location: Kentucky
Member Is Offline
Mood: No Mood
|
|
Wait a minute. Isn’t decarboxylation the same as thermal decomposition? Or am I missing something here?
|
|
|
DavidJR
National Hazard
Posts: 908
Registered: 1-1-2018
Location: Scotland
Member Is Offline
Mood: Tired
|
|
Quote: Originally posted by ELRIC  |
Wait a minute. Isn’t decarboxylation the same as thermal decomposition? Or am I missing something here? |
You could consider a thermal decarboxylation to be thermal decomposition, but there are of course other ways in which compounds can undergo thermal
decomposition which are not decarboxylation.
|
|
|
ELRIC
Hazard to Others
Posts: 244
Registered: 23-2-2015
Location: Kentucky
Member Is Offline
Mood: No Mood
|
|
Right. I was talking about ASA though. Can’t you also do this with KOH? I guess that would be another way that wouldn’t be a thermal decomposition
|
|
|
CuReUS
National Hazard
Posts: 928
Registered: 9-9-2014
Member Is Offline
Mood: No Mood
|
|
wouldn't that give phenol instead
of phenyl acetate ? (although ester hydrolysis would require water,whereas you are referring to alkali fusion)
hunterman ,there is a way to convert salicylic acid to phenol -https://www.youtube.com/watch?v=rovdf7REEU0 ( this kid claims he got 89% yield ,but both doug and nile red got a yield of 38% and 44%
respectively.Nile red later improved the yield to 51% in another video)
SM procedure -http://www.sciencemadness.org/talk/viewthread.php?tid=27617
Maybe you could try this for ASA ? the only thing I would be worried about is a fries rearrangement (I know it requires a lewis acid,but still)
|
|
|
Hunterman2244
Hazard to Others
Posts: 105
Registered: 6-6-2018
Member Is Offline
|
|
| Quote: Originally posted by CuReUS | wouldn't that give phenol instead
of phenyl acetate ? (although ester hydrolysis would require water,whereas you are referring to alkali fusion)
hunterman ,there is a way to convert salicylic acid to phenol -https://www.youtube.com/watch?v=rovdf7REEU0 ( this kid claims he got 89% yield ,but both doug and nile red got a yield of 38% and 44%
respectively.Nile red later improved the yield to 51% in another video)
SM procedure -http://www.sciencemadness.org/talk/viewthread.php?tid=27617
Maybe you could try this for ASA ? the only thing I would be worried about is a fries rearrangement (I know it requires a lewis acid,but still)
|
That is more or less what inspired me. According to the Wikipedia page for phenyl acetate, this should work. Maybe even as a one pot synthesis to
phenol.
[Edited on 15-8-2018 by Hunterman2244]
[Edited on 15-8-2018 by Hunterman2244]
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
