5 grams bromovanilline were refluxed with 25 mg Cu and 9 grams Naoh to obtain hydroxyvanilline.
after 8 hours the mixture was acidified with Hcl until Ph 2.
non polar solvent was added (ether). Mixture was just a little bit shaked.
3layers forms:Up layer is yellow transparent(Ether and hydroxyvanilline?)
Middle layer is orange (aqueus no organic).
On bottom layer there is a mass of precipitate (unreacted bromovanilline?).
Please help.