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.
Oxy - 7-6-2021 at 13:11
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]SuperOxide - 7-6-2021 at 14:42
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.clearly_not_atara - 8-6-2021 at 09:05
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.SuperOxide - 8-6-2021 at 10:56
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.
