I have carried out a reaction with hydrazine expecting a product with a phenolic substituent with three hydroxyl groups (two ortho and one para), but the para hydroxyl is lost in the product.
You could imagine making the keto tautomer from the Phenol. This would then undergo Wolf-Kishner type reduction and rearomatisation to give you the dehydroxylated compound.
Thank you very much Matthew. I thought about it, but I was wondering whether it reduces to a methylene or a 20 alcohol. For rearomatisation it should be a 20 alcohol so that it restores aromaticity by loss of a water molecule. If it reduces to a methylene, how does it oxidise back to an alcohol?
I can also see a possibility of it rearomatising by loss of nitrogen and hydrogen from an imine, is it physible?
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