Chemistry Forums for Students > Organic Chemistry Forum
Styrene
rolnor:
You could try catalytic p-TSA, reflux in toluene. I dont think you should do it neat. You can use a Dean-Stark trap. Its problematic to separate toluene and styrene, thats a drawback.
Orcio_87:
@Humr Be careful as the styrene can polymerize in the presence of strong acid (H2SO4).
Humr:
Thanks for suggestions. I can try the idea with p-TSA or try to modify http://www.orgsyn.org/demo.aspx?prep=CV3P0204 .
Also i found some reactions on reaxys for decarboxylation of cinnamic acid
wildfyr:
Styrene can do cationic polymerization initiated by a strong acid like pTSA or sulfuric acid, though it will be a mess.
Decarboxylation of cinnamic acid seems a little nicer... but what about doing the classic markonikov addition of an OH if you're trying to spread your wings? Mercuric acetate and water followed by NaBH4 is right out of sophmore organic.
rolnor:
I have done this type of elimination with p-TSA, this was 1-phenyl-1-isopropyl methanol so its very similar, it worked fine. H2SO4 is probably to strong, I agree with you on that wildfyr. One problem with this synthesis is that styrene is volatile, distillation will be the only way of purification.
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