Sciencemadness Discussion Board

base induced saponification of 3,4 methylenedioxyphenylbutene-2-one enol ester

jon - 2-7-2007 at 20:40

I was looking at a previous thread where someone supposedly took some piperonal and condensed it with mek to get the phenylbutene-2-one and then did a bayer villiger oxidation on it to get the enol ester which he then hydrolysed with NaOH in alcohol and water (50/50).
this is my question, the saponification was done at room temp. would'nt lower temperatures just favor aldol products? would it rather be advantageous to raise the temperature to reverse any aldol condensations?
I ask because I know the aldol condensation is a reversible reaction and usually done in the cold since this is the thermodynamic product. the reason it was done with base and not acid is because of that aryl ether that is sensitive to hydrolytic cleavage.

[Edited on 3-7-2007 by jon]

[Edited on 3-7-2007 by jon]