9-anthraldehyde purification as bisulfite adduct.
Hello! Long time no see huh? I wonder if anybody remembers me.
I have performed Vils Meyer on anthracene hoping to get some 9-anthraldehyde as of the protocol attached. Instead of POCl3 I have used SOCl2 because
of it being around and haven't gotten satisfying results. I don't really know how much difference does it do in this particular case, but as far as I
know they're more or less replaceable.
My product doesn't seem to be that pure, having melting point way higher than the literature 106C (around 160) which makes me think that a lot of
starting anthracene hasn't reacted and being pretty unreactive towards Wittig condensation.
I want to purify the aldehyde by making a bisulfite adduct, which seems the easiest way.
I have stirred it in pretty concentrated metabisulfite for few days, but only what I have got was a solution, that upon addition of Na2CO3 hasn't
given anything at all, even with boiling. Addition of NaOH resulted in orange solution and some minuscule amount of yellow powder all of which has
probably undergone canizzaro overnight losing its colour.
Now I want to ask you about the adduct formation of such bulky aldehyde which is 9-anthraldehyde.
What reaction conditions are preferable and is it even possible practically? Please give me some tips, would refluxing in the bisulfite soln. Help?
[Edited on 9-4-2023 by mackolol]
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