PeetPb
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phenylacetylene from styrene
Hi ,
I saw a method how to prepare phenylacetylene from styrene. It's based on bromination of the double bond and then elimination by a base like NaOH. The
problem is that I can't get elemental bromine. Or better said, I could get it but I'm a little afraid of it. Could I use chlorination for this ? or is
there another way?
thanks
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DJF90
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You could always generate the bromine in situ, using say HBr and H2O2. Alternatively you may try dilute acid, a bromide salt and an oxidising
agent.
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Nicodem
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Thread Moved
25-6-2012 at 03:09 |
PeetPb
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thanks I'll try to improvise somehow ....
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Adas
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I would assume that when you react NaOH with 1,2-dibromo-1-phenylethane, you will get 1,2-dihydroxy-1-phenylethane. You would probably need a strong
dehydrating agent.
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Nicodem
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| Quote: | | I'll try to improvise somehow .... |
To improvise anything you need to have comprehension of how things work. If you want to have a minimum chance of success I rather suggest you to hit
the literature. To give you a starting point, see DOI: 10.1016/j.tet.2009.03.034
Quote: Originally posted by Adas  | | I would assume that when you react NaOH with 1,2-dibromo-1-phenylethane, you will get 1,2-dihydroxy-1-phenylethane. |
Based on what reference? I can't really figure out why would you so naturally assume something that goes against the current level of theory?
We even have a domestic reference that goes contrary to what you say: Preparation of Styrene and Phenylacetylene from Polystyrene
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solo
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Reference Information
Environmentally benign electrophilic and radical bromination ‘on water’: H2O2–HBr system versus N-bromosuccinimide
Ajda Podgoršeka, Stojan Stavbe
Tetrahedron
2009, Volume 65, Issue 22, 30 Pages 4429–4439
http://dx.doi.org/10.1016/j.tet.2009.03.034,
Attachment: phpZaCeJq (790kB)
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