Sciencemadness Discussion Board

1-Iodo-3,4-Methylenedioxybenzene from sesamol?

ChemistryGhost - 19-3-2013 at 14:36

Can 1-Iodo-3,4-Methylenedioxybenzene be obtained from sesamol? Reacting sesamol with Phosphorus Triiodide? Or another way from sesamol. :P I think it can be done with HI, but will PI3 work?

[Edited on 19-3-2013 by ChemistryGhost]

[Edited on 19-3-2013 by ChemistryGhost]

turd - 20-3-2013 at 07:03

You would probably be better off by starting with 1,3-benzodioxole, which should be cheaper (an important factor given that you will not get excellent yields). Or even more amateur friendly: start from catechol - I'm not sure we have a reliable OTC methylenation reaction floating around?

Just a heads up: If you plan to turn the iodo compound into the phenylacetone using the acetylacetone method, you might run into troubles with separation from side products: https://www.sciencemadness.org/whisper/viewthread.php?tid=20...
;)

Nicodem - 20-3-2013 at 07:18

Quote: Originally posted by ChemistryGhost  
Can 1-Iodo-3,4-Methylenedioxybenzene be obtained from sesamol?

Not in any single step or any practical multi-step route. Sesamol can be O-triflated and the sesamol O-triflate could potentially be transformed to 5-iodo-1,3-benzodioxole with Pd or Ni catalyzed substitution. But why would anybody bother with something as expensive, irrational and difficult when the same product can be obtained in a (probably already published) single step from the relatively inexpensive 1,3-benzodioxole?

Quote:
I think it can be done with HI, but will PI3 work?

I can't see what makes you believe any of this. I'm sure that if you will invest some effort to read any basic organic synthesis book, you will be able to realize the nonsense contained in the quoted sentence.