transformation of HOOC-Ar-CHO to HOOC-Ar-CH2OH
Ar = Aromatic ring
Thanks in advance!
I would have thought a brief treatment with NaBH4 would have sorted this out. Keep the reaction times short and the reactions cold if you have to. Failing that you may be able to reduce the aldehyde via a hydrogenation reaction.
Good Luck
Thank you all very much. So there is no need to protect the carboxylic acid via esterification etc?
Dumitru: esterification won't help. Esters are reduced very similarly as free carboxylates. If you want to protect them from the reducing agent, then you really need to mask the carbonyl functionality, similarly to protecting of ketones with e.g. diols.
exactly...esters are reduced to aldehyde as well by LiAlH4.....if u really wanna protect your COOH maybe you can go for an orthoester, base stable and cleaved under pretty mild conditions in two steps....anyway....as stated before, using a less strong reducing agent would for me be the way of choice..
Here the carboxylate shape protects itself because it is dense in electron. So no reduction of COOH with NaBH4.
You could use an alakline aqueous solution of NaBH4. Carboxylate anion wont react and workup will be easy.
The suggestion given in the very first reply by Luke is the way to go.
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