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.