Sciencemadness Discussion Board

Synthesis of betanitrostyrenes in aqueous medium

phazer1980 - 19-8-2015 at 04:21

Hello

Say I dissolve some benzaldehyde in the absolute minimum of ethanol and mixed it with methylamine gas and some nitroalkane dissolved in water and reluxed in for 4 hours AND the aldehyde and the ketone were both lower and liquids, would the condensation product, hopefully a betanitrostyrene, then precipitate as soon as it form, not being soluble in a water/ethanol mixture? Or would the presence of so much water inhibit the condensation so much that yields would be terrible?

I am trying to make the product fall out of solution as soon as it is formed both to make workup easier but also to drive the equilibrium to the right by removing on of the products as soon as it forms, and if I combine this with a Dean stark setup to remove the second major product, water, then one could maybe achieve quantitative yields.

What if I used other solvents that the nitrostyrene is not very soluble in? Any suggestions?

Also to remove water without a dean stark setup I have though about having a teabag of MgSO4 in the reaction mixture as free drying agent would mix with the product falling out of solution. If I use the teabag in a solvent that MgSO4 is not at all soluble in wouldn't that work? removing water must giver better yield according to the math anyway.

What do you experts think?

j_sum1 - 19-8-2015 at 04:27

Hi phazer.
I don't know the answer to your question so can't help you much there.
It is board etiquette to put all threads without a reference in Beginnings. It sounds like you are following some procedure that you have read here. If you post your source you will get a better quality of reply.
Welcome to SM.

gdflp - 19-8-2015 at 06:26

It is painfully obvious what you are trying to do, and that you have little to no knowledge of chemistry. I would recommend you follow one of the many writeups elsewhere on the web. Sciencemadness is not the right place for you.

Bert - 19-8-2015 at 06:45

I'll let Nicodem kick this one to the kerb if he feels the thread deserves it-

In the meantime, please keep it in beginnings unless you include references or describe actual work you have done.

byko3y - 20-8-2015 at 07:37

Use NaOH as the only basic catalyst. Follow this procedure http://www.orgsyn.org/demo.aspx?prep=CV1P0413 . Tell us about your results.