Sciencemadness Discussion Board - Trying to synthesize 1-iodobutane

Trying to synthesize 1-iodobutane

siam65 - 3-11-2016 at 05:47

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?

Meltonium - 3-11-2016 at 06:34

You just need a proton donator. Strong acids are usually the easiest to use.

Justin Blaise - 3-11-2016 at 18:31

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...

CuReUS - 4-11-2016 at 01:14

how about using Al foil,I₂ and n-butanol ?

siam65 - 4-11-2016 at 02:54

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.

NitreRat - 4-11-2016 at 08:18

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.

CuReUS - 5-11-2016 at 00:31

Quote: Originally posted by siam65

Actually i cannot use elemental iodine in my reaction.

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

NitratedKittens - 28-11-2016 at 01:47

Could HCl + KI + Butanol work via the following mechanism:

CuReUS - 28-11-2016 at 02:15

Quote: Originally posted by NitratedKittens

Could HCl + KI + Butanol work

Quote: Originally posted by siam65

is it possible to prepare the same product without using any strong acids?

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

NitratedKittens - 28-11-2016 at 04:47

Oops, didn't see the strong acids part