Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: faust on October 29, 2005, 05:22:30 AM

Title: NMR : question of solubility
Post by: faust on October 29, 2005, 05:22:30 AM

Hello,

I have a little problem.

You can see my reaction on the following picture.

i'm sure of the structure of my reactant. So I heated during one night my ester in an EtOH/NaOH solution. Then I added HCl and a I got a withe solid which I suspect is my acid be cause it is only soluble in a KOH solution.

But I have some problem in NMR... how can I dissolve this acid? I tryed CDCl3, CD3OD, D2O and it is only slightly soluble in DMSO... but the NMR 500 MHz see nothing except the DMSO signal...

So , if you have an idea... you're welcome!

Title: Re:NMR : question of solubility
Post by: Winga on October 29, 2005, 06:47:05 AM

Try to use a deuteriated solvent with both polar and aromatic ends.

Title: Re:NMR : question of solubility
Post by: Mitch on October 29, 2005, 07:28:59 AM

Get a mass spec. as well, so you don't waste your NMR time.

Title: Re:NMR : question of solubility
Post by: faust on October 30, 2005, 04:28:32 AM

Thank you very much!

You're may be right... I hope this is my final acid which precipited...

I'll send a mass spec form tomorow

Title: Re:NMR : question of solubility
Post by: movies on October 30, 2005, 12:43:48 PM

You might also try deuterated acetonitrile or pyridine.  Both are pretty expensive, so far as deuterated solvents go, but they are actually really nice NMR solvents.