Hunterman2244
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Aspirin to phenyl acetate
Is the any way to convert ASA to phenyl acetate?
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CuReUS
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http://pubs.rsc.org/en/content/articlelanding/2012/cc/c2cc33...
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Hunterman2244
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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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Sci-hub.tw
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Hunterman2244
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Thanks!
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clearly_not_atara
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I'd guess you could get some kind of result by refluxing it in acetonitrile with CuI and maybe pyridine.
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Hunterman2244
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Could it be done by decarboxylation?
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clearly_not_atara
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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?
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Hunterman2244
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I meant decomposition. Like heatwise
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ELRIC
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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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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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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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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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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)
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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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