I am doing a separation scheme of4-chloro-3,4-dimethylnonane-1-amine and4-hodroxy-3-methoxybenzaldehyde (which I think is vanillin). Ibelieve both are starting as a solid. The first molecule andvanillin should be soluble in diethyl ether, while vanillin issoluble in water as well (but the first molecule is not). Would Ijust need to add water and use gravity filtration, then make thevanillin solid again? I've thought about dissolving both in etherthen adding HCl to change the solubility of the first molecule, butI think Vanillin would also react with HCl and both would still bemixed together.