Hi
I am asking if possible to do Michael addition of ethanol to acrylic acid or ethyl acrylate and if possible such reaction what cat i need that
Ths for reply
No, it is doubtful. Hydroxyl groups do not ionize easily pKa = 16 meaning you'll need sodium metal to rip away the hydrogen in order to make the oxygen into a nucleophile. Michael additions require 'soft' addition conditions. So the answer is no, but EtMgBr should work.
Thank you for reply! I am wondering what could be the product of reaction betw sodium ethoxide and sodium salt of acrylic acid for example:
EtO:Na + CH2CHCOO:Na = EtO-CH2CH(Na)COONa ? May be not right but only this could imagine:)
Very interesting sugestion with the Grignard reagent but i am still learning these reactions;)
C2H5MgBr + CH2CHCOONa = ?
Continue thinking...
Well the you should use a methyl ester so the sodium metal should be omitted.
Solvents include a minimum of diethylether (not THF) for preparation of the Grignard reagent. Then the CH2:CHCO2Me should be added dropwise in DCM or toluene or petroleum ether? A catalytic amount of Cu(I)Cl is also encouraged.
Temperature is strongly connected to the thermodynamics and kinetics of the reactivity towards the soft vs. hard addition sites.
The above document gives alot of information and the conditions will depend on the nucleophile chosen. It is an extremely complex reaction though making it diffcult to decipher the exact conditions needed.
Ths for the good article. But my primary aim is to obtain C-O-C bond using Michael addition reaction... I realize its not very good idea with alcohols and may be the classical Williamson synthesis is better for thus purpose. Any ideas for C-O-C bonding reactions(also with acrylates;) are welcome.
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