siam65
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Trying to synthesize 1-iodobutane
Trying to make 1-iodobutane from potassium iodide and n-butanol. While using strong acid like phosphoric acid desired product was successfully made...
the question is, is it possible to prepare the same product without using any strong acids?
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Meltonium
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You just need a proton donator. Strong acids are usually the easiest to use.
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Texium
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Thread Moved
3-11-2016 at 06:47 |
Justin Blaise
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If you can turn the alcohol into a leaving group, you can do an SN2 to get your iodide. If you can get your hands on some triphenylphosphine and
iodine, you can run an Appel-type reaction.
http://www.organic-chemistry.org/namedreactions/appel-reacti...
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CuReUS
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how about using Al foil,I2 and n-butanol ?
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siam65
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Thanks everyone...
Actually i cannot use elemental iodine in my reaction.  ..actually i am getting
potassium iodide as a side product of a different reaction in which iodobutane has been used as a reactant along with butanol. So i want to regenerate
iodobutane from potassium iodide and butanol.
About the appel reaction...will it work if i use KI instead of iodine?
Also curious about using Aluminium foil.
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NitreRat
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There are loads of different easy-to-aquire oxidizing agents that can oxidize KI into elemental iodine. Have you investigated any of those reactions
as a potential possibility? It might be much simpler/cheaper than acquiring triphenylphosphine.
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CuReUS
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Quote: Originally posted by siam65  | | Actually i cannot use elemental iodine in my reaction. ..actually i am getting
potassium iodide as a side product of a different reaction in which iodobutane has been used as a reactant along with butanol. So i want to regenerate
iodobutane from potassium iodide and butanol. |
IMHO,you need some kind of a catalytic oxidation cycle that will convert KI to I2 which can then react with Al and n-butanol to form
iodobutane.
As nitrerat mentioned,there are tons of oxidants out there.But unless you tell us more about your reaction(in which KI is being formed),we can't tell
you which oxidant is the most suitable for your reaction
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NitratedKittens
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Could HCl + KI + Butanol work via the following mechanism:
Basket of kittens for you ........BOOM
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CuReUS
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one thing the OP could do is to add ammonium persulfate or the K salt of that along with Al foil into the reaction mixture.The persulfate would
oxidise the KI to I2 which would then react with Al and n-butanol to form iodobutane
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NitratedKittens
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Oops, didn't see the strong acids part
Basket of kittens for you ........BOOM
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