liftedresearch
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Alpha Ethylstyrene
Hello all,
I have looked far and wide for a synthesis of alpha Ethyl styrene, but to no avail. I'm not looking to be spoon fed, just to be pointed in the right
direction, and help at all would be greatly appreciated. Thanks in advance
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MeshPL
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That's tricky. Could you please list all reagents that are available to you? I have some ideas, the "simplest" (few steps but unusual, hard to come by
reagents) one is:
Benzene + Propionyl chloride -AlCl3-> Propiophenone
Propiophenone + Tebbe's reagent/Appropraiate Wittig reagent/Petasis Reagent/TiCl4 + Nysted reagent -> Alpha-ethylstyrene
(The latter can be done in numerous ways, there is a wide choice of reagents, none of which have any use for an amateur )
[Edited on 5-2-2016 by MeshPL]
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PHILOU Zrealone
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Benzene + CH3-CH2-CHCl-CH2OH + AlCl3 --> C6H5-CH(-CH2OH)(-CH2-CH3)
C6H5-CH(-CH2OH)(-CH2-CH3) -acid dehydration like H2SO4 or formic acid/heat-> C6H5-C(-CH2-CH3)(=CH2)
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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CuReUS
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you could make this compound in two ways
method 1
acetophenone to the 2-phenylbutan-2-ol
(a) using grignard ( 95 % yield) - Zong, Hua; Huang, Huayin; Liu, Junfeng; Bian, Guangling; Song, Ling Journal of Organic Chemistry, 2012 , vol. 77, #
10 p. 4645 - 4652
(b) using lithium reagent( 92 %)-Imamoto, Tsuneo; Kusumoto, Tetsuo; Yokoyama, Masataka Journal of the Chemical Society, Chemical Communications, 1982
, # 18 p. 1042 - 1044
2-phenylbutan-2-ol to alpha ethylstyrene (83 %) - http://www.tandfonline.com/doi/abs/10.1080/00397910008087423
method 2
phenylacetylene to alpha ethylstyrene( 98%) -http://onlinelibrary.wiley.com/doi/10.1002/recl.19811000305/...
but I found something funny, there is a discussion for the synthesis of alpha ethylstyrene on the Hive
http://chemistry.mdma.ch/hiveboard/chemistrydiscourse/000363...
[Edited on 6-2-2016 by CuReUS]
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MeshPL
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Dehydration of 2-phenylbutan-2-ol will MOSTLY yield 2-phenylbut-2-ene. That's due to stability of internal vs. terminal alkene.
Philou's Friedel-Crafts alkylation may be a better idea. Although 2-chlorobutan-1-ol may be hard to make, it is sure easier to come by than weird
reagents I mentioned.
[Edited on 6-2-2016 by MeshPL]
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CuReUS
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if you are going by the grignard route,you could also react phenylMgBr with MEK to get the tertiary alcohol
meshPL , the paper said that you would get the terminal alkene not internal,even in philou's method,what's stopping the double bond from resonating
from terminal to internal after the dehydration step ?
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MeshPL
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Sorry, my bad. Although I can't view the paper anyway, for some reason. Weird, that in that case more stable alkene is terminal.
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chemrox
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I have some somewhere if you want to buy a few ml...
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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