The idea is to lower the rxn times with an higher yield by useing pyridine for the hydroxylation of 5-br-vanillin.
I hope scravenging the halogen from the benzene ring via pyridine to form a cation which is open for the atttack of OH-
Swim added 15grms (n mole) of the aldehyde to 200mls H2O and trace of Cu powder (dunno why?). Then he measured 8mls (>n mole) of pyridine and added it to the suspension. Visible rxn formed a grayish solution with a white preticipate. Then 18gms of NaOH was measured, dissolved in 80mls H2O and added to the rbf while still hot. A visible rxn occured and the solution became orangeish. Then started refluxing under inert atmosphere. Still going on, planning for 3 hours.
Q. Can pyridine scravenge the 5- halogen and ease the attack of OH- ion?
Maybe using acetonitrile as a solvent, first refluxing the halo-ald. w/ pyridine then decomposing w/ OH- might be better?
Please help! I cant bear experimenting for days without any referenced mechanism and real result
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