[malviyangr]

Hi, i tried to do the claisen condensation reaction between aromatic ester and ketone using NaH in distilled THF as well as in Lithium amide in ether but none of the two above gave the positive results.....something is wrong, but am not able to find out....can anyone plz tell what precautions should be taken ?
which base will be better to use lithium amide, sodium amide, sodium hydride?? and plz also suggest the suitable solvent among THF/Toluene/ether???
thanks 4 any help....!!!!!!!!!!!!

[Arctic-Nation]

When you say that you got no positive results, are you observing no reaction, self-condensation of the ketone or possibly even decomposition of a reagent, or something else? Finding out how and where your reaction goes wrong will enable you to fix it.

[malviyangr]

I used Lithium amide in ether, added aromatic ester, ketone into it and refluxing was done at 50 deg for 15-20hrs.. then, we added water to it to hydrolyse. According to us , our compound (lithium salt of diketone) should be soluble in water...so, we extracted water layer from the mixture. then added acetic acid to the water layer in order to get back the compound...but no compound was separated even oil was also not found . I am not getting it..where am i wrong at which stage? I have tried this reaction number of times by adding ketone first to the mixture of lithium amide in ether then added ester to it. I have also tried in other way round that ester was added before the addition of ketone to the mixture of lithium amide in ether..
Even, i have also used the other solvent condition i.e in distilled THF instead of ether but sodium hydride was used as a base in this case, the same thing happened in this also after addition of acetic acid. nothing was obtained.
 how could i make out at which stage - i am wrong??
Please give some suggestions!!!!!!!!!!!
I am a beginner. I have read many literatures regarding the above reaction, but none of them worked please suggest me some good literature on claisen condensation which can help me out in the growth of my research.

[Doc Oc]

I doubt that compound is water soluble.  Ketones and esters aren't super water soluble, but you also have an aromatic ring that acts as a big slab of lard.  I can almost guarantee you that's in the organic phase.  This should be easy to verify by TLC.