My reactants are not consumed and no new product spot is formed. My reaction conditions include dissolution of the acetophenone and aldehyde derivative in ethanol followed by dropwise addition of the 40% KOH solution. The reaction was run at room temperature and heating at 55 degree Celsius as well. Any inputs would be appreciated!
Hi Neha Nambiar , could you elaborate a bit further on the nature of your starting aldehyde?
Did you use freshly distilled aldehyde to make sure no corresponding carboxylic acid remains in your starting material?
Hi Lukas Martin Holz , thank you for your response. I'm using a trihydroxy substituted aromatic aldehyde as obtained from the manufacturer. Just checked an NMR of the compound and it seems to be pure.
Ok. How many equivalents KOH are you using? Typically such aromatic aldol condensations are run with catalytic amounts of base. I guess your triphenolic aldehyde reacts first with any base you throw at it, forming the phenolate, before the KOH hast any chance of deprotonating your ketone.
I would use the trimethylated aldehyde for the aldol condensation and deprotect the methyl groups afterwards.
Alternatively, you could use an excess of KOH and run the reaction at higher temperatures, e.g. at EtOH reflux.
Lukas Martin Holz I'm using the base in excess but it doesn't seem to be working. I would definitely try running it under reflux conditions. Thanks a lot for your inputs!