I have a synthesis where I need to attach a vinyl group to a phenyl group. I'm using toluene and 3-chloro-1-propene as a model system, under Friedel Crafts alkylation conditions. Would I expect to create vinyl toluene or is there going to be a rearrangement that will produce something other than vinyl toluene?
Jensen,
You would like to prepare vinyl toluene, is that right ! vinyl group is two carbons CH2=CH- and you are starting with 3-chloro-1-propene, a compound of three carbon atoms !. So of course you will get something else !
I would like to draw your attention to
---http://revroum.getion.ro/wp-content/uploads/2006/RRC_9_2006/art5.pdf and references therein
Good luck
Thank you Amer. I was thinking the reaction wouldn't be straight forward. I think I'll change my conditions and look at a dehydration reaction of something similar to dehydrating 1-Phenylethanol with H2SO4.
Or maybe I'll look into doing an elimination reaction using (1-Bromoethyl)benzene or (2-bromoethyl)benzene using t-butoxide.
Do you have any benzaldehyde? You can look for the synthesis of styrene and try to apply it to your system.
Ruben, I can't find anything according to your recommendation. I do find methods to convert styrene to benzaldehyde but nothing to convert benzaldehyde to styrene.
You can try a Wittig reaction between a benzaldehyde and methyltriphenylphosphonium iodide (this is prepared in a rection with methyl iodide and triphenylphosphine). A different method could be the reduction of acetophenone and finally a dehydration step
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