[sommy]

I have repeated the acrylation (4 times) of OH groups in Acetone (in the presence of triethylamine and DMPA) several times and usually there is tiethylamine hydrochloride salt which I filter it. but this time, just like the other time, the salt was being produced at first and the solution became milky, but after an overnight, the salts were gone! I don't get it what happened to the salts? there is no water in the reaction, there might be some unreacted carboxylic acids but even if there is it needs heat anc catalyst to react with OH groups and make water! does anyone have any idea?!

[Archer]

Triethylamine is extremely hygroscopic, it may have absorbed atomspheric water.

In my experience the acetone does not have to be too wet before it will dissolve some amine hydrochlorides. On the other hand in some cases, adding acetone to saturated amine salts often removes the water anf gives the solid salt again.

Did the reaction work? were you able to isolate your product in the same yield as before?

[sommy]

Archer! thank you for your reply! the reaction was under N2 (the same cylinder), so it cannot absorb water! I still have to do the extractions to know if it worked or not, I'll write the results here, whenever it's done.

[Archer]

Archer! thank you for your reply! the reaction was under N2 (the same cylinder), so it cannot absorb water! I still have to do the extractions to know if it worked or not, I'll write the results here, whenever it's done.

Thank you for yoru reply, do please keep us posted.

Did you use the same batches of reagents and solvent for each reaction?