Synthesis of Benzaldehyde and Aniline Schiff Bases I have a problem while synthesize the schiff base. I synthesized using absolute ethanol as solvent and use reflux method for 4 hours generally. The problem occur on TLC where there is still two spot on the product which one of them are very clear (top one) (which I guess the ligand formed) and another one were very light, while on NMR spectra, whereby there is a singlet peak at approximately 10.0 ppm which I assumed that it is from the aldehyde itself which probably not completely reacted. I also tried several derivatives based on benzaldehyde and aniline but some of them have to be recrystallize which I havent found the suitable solvent system yet.

So with all due respect, I really need help especially those who have an experience on synthesizing schiff base and also share to me some ideas to recrystallize my ligands.
The reaction needs acid catalysis but ethanol is fine as solvent. There will always be some starting materials left, but since the product is a solid and the reagents are liquid, the best (and cheapest) is to purify it through recrystallization. 

For this, dissolve the product in the smallest quantity of hot ethanol and then add water until precipitation occurs.