Sometime TLC and column chromatography becomes hard. So, distillation with/without vacuum could be easy to separate the product from the mixture. The more temperature difference among the chemicals the best or easier the procedure. However, if there would anyway to predict the product boiling point, it could be useful.

How to predict the boiling point of the product while the boiling points of reactants are known and how the new bond effect on the product? Any literature is highly appreciated.

An example of a reaction is given in the picture.