The Vespiary

The Hive => Methods Discourse => Topic started by: chilly_willy on December 15, 2003, 01:21:00 AM

Title: possible OTC p2p..?
Post by: chilly_willy on December 15, 2003, 01:21:00 AM

Something caught my eye about the chloramine T + Na, K iodide..look here:

Post 303014 (https://www.thevespiary.org/talk/index.php?topic=9871.msg30301400#msg30301400)

(cesium: "5-iodovanillin (Chloramine T + NaI)", Methods Discourse)
If you look at the structure of vanillin..its just a really decked out benzene ring.  This particular prep seems like it adds iodine gently to the benzene ring..so Im (guessing) that it should have no problem adding to just benzene...forming iodobenzene.  Ok so if it works you have iodobenzene. You can then work from this p2p prep here:

Post 470750 (missing)

(Rhodium: "Cognate Preparation", Methods Discourse) and

https://www.thevespiary.org/rhodium/Rhodium/chemistry/p2p.acetylacetonate.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/p2p.acetylacetonate.html)

If you use the prep from

Post 470750 (missing)

(Rhodium: "Cognate Preparation", Methods Discourse) word for word except for CuCl instead of CuI (cheaper), Na or K carbonate (cheapest)...up to 80% yeilds can be had in one reaction in 4-8 hours!  Its almost like a benzo wacker with iodobenzene..right?  The only hurdle might be the acetylacetone which seems like a pain to make from the 2 synths from orgsyn...  If this can all be confirmed can someone maybe post about a suitable prep for acetylacetone??  ;)   Thanks!

CW
8)

Title: if iodobenzene can be formed this way
Post by: Organikum on December 15, 2003, 02:10:00 PM

whereabout I am absolutely not sure as substituted compounds are easier monohalogenated as nonsubstituted ones as I remember than you should look for antoncho + zealot + zinc in the FSE for a much more conveniant synth from iodobenzene to P2P.

Title: may bee of some use
Post by: jemma_jamerson on January 22, 2004, 09:42:00 AM

Post 231411 (https://www.thevespiary.org/talk/index.php?topic=12302.msg23141100#msg23141100)

(epistemologicide: "can this work", Serious Chemistry)

Title: iodobenzene
Post by: hypo on January 22, 2004, 10:57:00 AM

> if iodobenzene can be formed this way

well, the article says "iodination of phenols", so draw your conclusions...

but iodobenzene is trivial anyway.
benzene + iodine + sodium persulfate => iodobenzene, 70% from iodine.
sodium persulfate can be had in every electronics shop for cheap

Title: ReA: possible OTC P2P
Post by: java on January 22, 2004, 05:49:00 PM

Hypo  I found both benzene and Iodine either hard to get ; cancer associated with benzene and Iodine watched . I hence looked around and posted this method to synthesise Iodobenzene ,
Post 482049 (not existing)
and in the thread Rhodium posted a procedure from organic synthesis.......also, this along with acetone enol in dmso will get you to p2p ...see in the search engine under enols and find out more if it interests you.....java

Title: perbenzoic acid?
Post by: Vitus_Verdegast on January 22, 2004, 11:10:00 PM

Speaking of iodobenzene, does anyone have more information on what the late Halfapint suggested?

---

Drone's acetone enolate route to P2P with iodobenzene deserves another look, now we know potassium isopropoxide is available through adding KOH to isopropanol and running CaO through it. That should prove a strong enough base to get the job done, though sodium ethoxide is not. Jerry March has a remarkable route to iodobenzene by treating perbenzoic acid with CuI. (Actually, he says "cupric iodide", but there is no cupric iodide, only cuprous iodide. Wrong there, Jerry. Cupric bromide works too, which I've made by simple exchange.) Perbenzoic acid we can get from benzoic acid and an OTC peroxide reagent, e.g. oxy-clean or Xxorox color-safe non-chlorine dry bleach, which contains sodium perborate, or of course oxone, without requiring H2O2 with all its water. You don't have to get benzene and halogenate it, just work through this route. This one, and perhaps the previous one, requires protection from air, though basically any anhydrous reaction does also.

---

Post 350684 (missing)

(Rhodium: "Half-a-Pint - RIP", General Discourse)

Title: diazonium chemistry
Post by: hypo on January 23, 2004, 09:48:00 AM

hi, java! i'm well aware of the (rich) aryl-diazonium chemistry.
i was just commenting on the first poster - it made me think that
(s)he has access to benzene/iodine.  :)

Title: Re: Environmentaly safe Iodobenzene ...
Post by: java on January 23, 2004, 10:49:00 PM

Here is an alternative to iodobenzene synthesis with the environment taken under consideration , besides it's cheap and easy.

Post 459094 (https://www.thevespiary.org/talk/index.php?topic=11931.msg45909400#msg45909400)

(java: "Re: Novel easy preparations of Iodobenzene.....", Novel Discourse)