SuperOxide
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Is it possible to synthesize phthalic acid [or anhydride] from phthalimide?
I'm well familiar with the synthesis of phthalic anhydride from phthalate based plasticizers, which I have done a few times. And I know that's easily
turned into phthalimide using urea or ammonia. However, I was looking to see if there's a known synthesis procedure for going the other direction? I
have a decent amount of phthalimide, and there are a few reactions I'd like to try that need phthalic acid/anhydride, and I don't want to have to
purchase them or make them again from scratch if I can just use the phthalimide I have on hand that's just been sitting on the shelf collecting dust.
I did look around, and either my Google fu isn't what it use to be, or there isn't too much out there about this.
Thanks.
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Oxy
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Carboxylic acids can be synthesised from amides by hydrolysis in acidic or basic conditions.
basic conditions will produce salt but it's pretty easy to convert it to acid
[Edited on 7-6-2021 by Oxy]
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SuperOxide
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Quote: Originally posted by Oxy  | Carboxylic acids can be synthesised from amides by hydrolysis in acidic or basic conditions.
basic conditions will produce salt but it's pretty easy to convert it to acid |
Thanks, Oxy. This looks right: http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch22/ch22-2... - I'll give that as hot.
[Edited on 7-6-2021 by SuperOxide]
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zed
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Hydrolysis of Phthalimide might not be really easy.
I'd look for a published procedure.
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Triflic Acid
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Amide hydrolysis is generally a pain. Might be worth trying http://www.sciencemadness.org/talk/viewthread.php?tid=79854
There wasn't a fire, we just had an uncontrolled rapid oxidation event at the power plant.
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SuperOxide
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Yeahhh, I did a little more research, it looks like it would be better to just re-make the phthalates, or buy some.
As always, thanks for the input.
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clearly_not_atara
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If you have hydrazine handy, phthalimide rapidly converts to the cyclic hydrazide. Then oxidizing this gives a 2,3-diazanaphthoquinone that should
easily undergo acidic hydrolysis. Nothing is easier than buying more, of course.
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SuperOxide
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| Quote: Originally posted by clearly_not_atara | | If you have hydrazine handy, phthalimide rapidly converts to the cyclic hydrazide. Then oxidizing this gives a 2,3-diazanaphthoquinone that should
easily undergo acidic hydrolysis. Nothing is easier than buying more, of course. |
Yeah, I saw this when I was researching the reaction. I don't have any hydrazine handy at the moment, though that's on my to-do list (maybe this weekend).
I may do it anyways (on a smaller scale) just as an experiment to learn about the reaction a bit.
[Edited on 8-6-2021 by SuperOxide]
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