I want to do di-alkylation on Active methylene (-CH2-) of diethyl malonate using sodium hydroxide (NaOH) only. Does any one have literature or a procedure?
Any reason you only want to use NaOH? In my experience NaH in DMSO would be best. You can download my DIC thesis from Research Gate which as some experimental procedures for mono and di alkylated malonates. If NaH is too expensive or hazardous you can use NaOMe (just be careful not to use too big an excess or you will get some transesterification). Hope this helps.
I think the pKa is probably ok, NaOH will be strong enough but I'm not sure that ethanol is the best choice of solvent. Depending on the alkyl bromide in question, putting the second alkyl group on might be a bit slow and DMSO will speed things along nicely and can also run at higher temperatures if needed. It really depends on substrates. NaOH in EtOH might work fine and is cheap, safe (but flammable) and convenient. But if reaction is slow or low yielding, head for the DMSO :)
Yes, you are right... EtOH is strong enought to protonate an anion of monoalkyl-malonate, so for dialkyl derivative it is better to use an aprotic inert solvent... I was thinking only about a base...:)
Ethanol and NaOH works well for ethyl malonate. Use methanol, instead, is you have methyl malonate. Always the same solvent as the ester used.
The ester CO CAN AND WILL be attacked by the nucleophilic alcoholate, so if you use a methyl malonate in ethanol, a transesterification will be produced, and you'll end up with a mixture of esters, depending on conditions used.