Alright, lets say someone creates a Schiff base from diethylamine and cyclohexanone in benzene, then dry p-toluenesulfonic acid in toluene is added to make the tosylate salt.. At this point, can the reaction mixture be brought to reflux to assure that there is no water in it, or would heat destroy the tosylate salt??

  Btw, is a 10 hour reflux of the p-toluene sulfonic acid monohydrate long enough to render it anhydrous?

  Will 10 hours of reflux dry the Schiff base?

  I'm talking about a 1 mole batch. Any suggestions would be much appreciated! Thanks. Peace!

just heat your 4-toluenesulfonic acid under the water trap until no more water seperates (use mag. stirring!) -> 3-4 hours are enough....

use dry acid, dry solvents and dry enamine (or it will decompose anyway), and dont reflux your salt!

Thanks for the heads-up! Is the 10 hour reflux for the enamine over-kill as well? As far as distilling off water goes, is benzene more efficient than toluene? Thanks again.