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Author: Subject: Aspirin to phenyl acetate
Hunterman2244
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[*] posted on 8-8-2018 at 20:57
Aspirin to phenyl acetate


Is the any way to convert ASA to phenyl acetate?
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CuReUS
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[*] posted on 8-8-2018 at 21:09


http://pubs.rsc.org/en/content/articlelanding/2012/cc/c2cc33...
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Hunterman2244
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[*] posted on 8-8-2018 at 21:13


Quote: Originally posted by CuReUS  
http://pubs.rsc.org/en/content/articlelanding/2012/cc/c2cc33...
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]
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Tsjerk
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[*] posted on 9-8-2018 at 06:02


Sci-hub.tw
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Hunterman2244
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[*] posted on 9-8-2018 at 06:21


Quote: Originally posted by Tsjerk  
Sci-hub.tw

Thanks!
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clearly_not_atara
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[*] posted on 9-8-2018 at 09:09


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]
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Hunterman2244
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[*] posted on 9-8-2018 at 14:58


Could it be done by decarboxylation?
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clearly_not_atara
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[*] posted on 9-8-2018 at 19:22


Quote: Originally posted by Hunterman2244  
Could it be done by decarboxylation?
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]
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Hunterman2244
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[*] posted on 10-8-2018 at 02:25


Quote: Originally posted by clearly_not_atara  
Quote: Originally posted by Hunterman2244  
Could it be done by decarboxylation?
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?
I meant decomposition. Like heatwise
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ELRIC
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[*] posted on 10-8-2018 at 07:38


Quote: Originally posted by Hunterman2244  
Quote: Originally posted by clearly_not_atara  
Quote: Originally posted by Hunterman2244  
Could it be done by decarboxylation?
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?
I meant decomposition. Like heatwise


Wait a minute. Isn’t decarboxylation the same as thermal decomposition? Or am I missing something here?
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DavidJR
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[*] posted on 10-8-2018 at 08:37


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.




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ELRIC
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[*] posted on 10-8-2018 at 11:15


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
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CuReUS
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[*] posted on 11-8-2018 at 00:24


Quote: Originally posted by ELRIC  
Right. I was talking about ASA though. Can’t you also do this with KOH?
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)
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Hunterman2244
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[*] posted on 15-8-2018 at 02:45


Quote: Originally posted by CuReUS  
Quote: Originally posted by ELRIC  
Right. I was talking about ASA though. Can’t you also do this with KOH?
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]
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