Author Topic: 1-iodo, 2-propanone possibilities?  (Read 1139 times)

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elfspice

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1-iodo, 2-propanone possibilities?
« on: May 01, 2004, 05:41:00 AM »

http://www.tau.ac.il/~phchlab/experiments/Acetone_iodination/


Iodination of Acetone

I found a reference to the use of bromobenzene and chloroacetone (the chloro version of the chemical produced from the above), the yields were fairly shitty though.

I have been trying to find out if there is a way to make iodo-benzene.

The route i'm looking at is working with phenol to make ethers and cleave with HI to yield Iodobenzene.

If one made sodium phenoxide and reacted with phenol, then distilled the diphenyl ether, then reacted the diphenyl ether with HI, would iodobenzene form out of the HI reaction with diphenyl eter?

I think from there the iodobenzene/1 iodo 2 propanone reaction should be fairly decently yielding, i think the weakness of the chloroacetone/bromobenzene reaction is that the halogens do not want to unite as a pair if they are different, and this would, i would think, promote the formation of the different haloalkanes joining into each other, in this case, 2,5 keto-hexane, and what happens to bromobenzene when it loses it's bromine next to another one which is also... phenyl benzene, that would mean only 1/3 of the reaction would result in the right combination because of the other two being more likely due to the formation of elemental halogen.

I think that the use of the same halogen should give a roughly 50% theoretical yeild of the desired compound because the mass action determines that if there is equal chance of reaction, that one biases the reaction in favour of the desired combination rather than bonding to the same halo-alkane.

there is four ways it can come out

phenyl iodide + phenyl iodide
acetone iodide + acetone iodide
phenyl iodide + acetone iodide
acetone iodide + phenyl iodide

I can't really say which one will rule the outcome but there might be a hinderance with the keto on the acetone, which would be the only problem.

THIS IS JUST THEORETICAL, i'm trying to find some new halogen based methods which make use of more easily available materials.


Rhodium

  • Guest
routes to iodobenzene
« Reply #1 on: May 01, 2004, 06:10:00 AM »
The route i'm looking at is working with phenol to make ethers and cleave with HI to yield Iodobenzene.

Won't happen. The only feasible routes to iodobenzene are:

* Post 482072 (not existing)
*

Post 380729

(pHarmacist: "Iodobenzene by direct benzene iodination", Novel Discourse)


Many variations on the latter theme is possible though, such as

Post 169606

(Rhodium: "Novel high-yield iodination method using I2/NaNO3", Novel Discourse)