[AlphaScent]

Hey all,

What is your preferred way to do a this procedure?  My compound is C14.  Is it too big to do this adduct?

I am trying to get unreacted aldehyde out of my product and ditillation is not working.

I added 0.5 eq of my aldehyde to a sodium bisulfite/water/EtOH system.   I am stirring for 45 min and then filtering and checking the organic by GC to see if the aldehyde has been removed. 

What do you guys think??  Am I a dummy??  I know about his process in theory, but have never done it in the lab.

Cheers

[discodermolide]

This should work but the C14 may mean it's not very crystalline. The tosylhydrazone derivative may be better as they may be more crystalline.

[AlphaScent]

@Disco,

If it is not very crystalline, then I guess it defeats the purpose huh.  I do not have any tosylhydrazine.

We shall see, lets hope it works.

[AlphaScent]

Well if its not very crystalline.  Could I partition the product between 50% sat. brine and ether.  The ionic character of the adduct (salt) should go into the polar brine and my desired material should go into the non-polar organic.. is this too good to be true?

[discodermolide]

That's worth a shot.
Chemistry is an experimental science!

[AlphaScent]

Touche.

[AlphaScent]

Well it worked to a certain extent.  By GC the peak has shrunken considerably.  Buy only by half on NMR.  Tomorrow is another day.. Ill let ya'll know tomorrow.

Cheers.