Sciencemadness Discussion Board

Mannich reaction

Nernst - 15-2-2009 at 08:10

I'm performing a mannich reaction and therefore I have to place dimethylamine.HCl and paraformaldehyde in my flask. I work with isopropylalcohol as a solvent. After these additions I place my keton in the flask followed by the addition of HCl.

Now I'm worried about the forming of bis(chloro)methylether. How big is the chance that there will form some bis(chloro)methylether out of paraformaldehyde and HCl?

chemrox - 15-2-2009 at 11:32

I just looked up an example that used the amine salt and I don't see an issue otherwise. I haven't used paraformaldehyde for this before. How is it unpoly'd in this case? Ah, I see numerous examples where it is used and it simply dissovles in the solvent system.

[Edited on 16-2-2009 by chemrox]

Nicodem - 15-2-2009 at 23:52

Quote:
Originally posted by Nernst
Now I'm worried about the forming of bis(chloro)methylether. How big is the chance that there will form some bis(chloro)methylether out of paraformaldehyde and HCl?

You don't have to worry about that.

rodanid88 - 12-9-2012 at 12:14

Does anyone know, what the mechanism is in this reaction: phenols or catechol react with formaldehyde and with primary or secondary amine. I know the first step is that you get the iminium ion, but after that? Probably it will do an electrophilic attack to the aromatic ring, but how?
Thanks