Sciencemadness Discussion Board

Purification of Carboxylic Acids (Knoevenagel)

gypsyNo2 - 5-6-2012 at 21:57

Hey Guys,

Am working on something at the moment and I am using a slightly modified Knoevenagel condensation to give me aromatic, alpha, beta unsaturated carboxcylic acids (http://dx.doi.org/10.1080/17518250802141200) and am having trouble purifying them.

I am reactting (all in molar eq) piperonal, malonic acid, ammonium formate in pyridine. Microwaved at 300W for about 2 minutes.

Have tried acid/base extraction but I keep getting this ultra fine powder which is hard to filer. have also tried simply washing the reaction contents with water but nothing seems to give me a decent looking compound (impurities galore).

Any ideas ?

Cheers

GypsyNo2

Hexavalent - 5-6-2012 at 23:58

Have you tried looking for a suitable solvent and recrystallizing your compound slowly?

gypsyNo2 - 7-6-2012 at 15:18

I have trialled a few, looks like DSMO/Water are a go but it tends to drop out as a powder which is just hard to deal with

Hexavalent - 7-6-2012 at 15:50

Sadly, that's the nature of some compounds.

You could also try cooling slowly in a gently warmed Thermos flask, or dissolve the compound into solvent and allow it to evaporate very slowly at RTP or maybe in a dessicator.

gypsyNo2 - 7-6-2012 at 19:51

Yeah cheers Hex, might give that a go, thanks mate.

Gyp

Hexavalent - 8-6-2012 at 13:21

You're welcome, give it a go and report back with your findings:)