I have a doubt about this synthesis
The reaction is made under basic conditioon in an aqueous /ethanol solution with NaOH.
After the adding of NaBH4 we get the vanillyl alcohol deprotonated ...so we use HCl in order to protonate it and getting the neutral vanillyl alcohol that with an ice bath it will precipitate
Now my question is why is this alcohol not soluble in a mixtures of H2O/EtOH and it will precipitate after a while??
because ,for example, example ethanol is soluble in water...we get mixture of both of them. It will not precipitate!!