[MissPhosgene]

Hello,

   I have to do a benzylic oxidation with IBX in DMSO and some fluorobenzene. Can I use the commercially available 45% wt IBX? It contains benzoic acid, 21-23%, and isopthalic acid, 28-30%. I was planning on following J. Am. Chem. Soc., 2002, 124, 2245-2258. In the supplementary information it is stated that they used commercially available materials without further purification. I am not sure if IBX was commercially available in 2002, but since the authors did not provide information on how it was made, it seems like that was the case.

I can make it, but would prefer to buy it if the purity level is okay.

Benzylic > allylic .

http://www.sigmaaldrich.com/catalog/ProductDetail.do?D7=0&N5=SEARCH_CONCAT_PNO|BRAND_KEY&N4=661384|ALDRICH&N25=0&QS=ON&F=SPEC

I'm scrolling through supplementary information sections of citing papers to see what other people have done.

[discodermolide]

Hello,

   I have to do a benzylic oxidation with IBX in DMSO and some fluorobenzene. Can I use the commercially available 45% wt IBX? It contains benzoic acid, 21-23%, and isopthalic acid, 28-30%. I was planning on following J. Am. Chem. Soc., 2002, 124, 2245-2258. In the supplementary information it is stated that they used commercially available materials without further purification. I am not sure if IBX was commercially available in 2002, but since the authors did not provide information on how it was made, it seems like that was the case.

I can make it, but would prefer to buy it if the purity level is okay.

Benzylic > allylic .

http://www.sigmaaldrich.com/catalog/ProductDetail.do?D7=0&N5=SEARCH_CONCAT_PNO|BRAND_KEY&N4=661384|ALDRICH&N25=0&QS=ON&F=SPEC

I'm scrolling through supplementary information sections of citing papers to see what other people have done.

I would purify it, you are liable to get esters by Fischer esterification. I assume you want the aldehyde?

[Doc Oc]

For what it's worth, I tried this procedure (to make the a,b-unsaturated ketone though, not for benzylic oxidation) and it didn't work at all.  A lot of that could be due to my technique though, I certainly wasn't experienced with those types of reactions, but the IBX I used was pure and it still didn't work.  I say try the lower grade stuff (especially since they say they did).  If I'm not mistaken, IBX is fairly inexpensive, it's DMP that really starts to hurt your pocketbook.

[discodermolide]

Why not use TEMPO/bleach? Or BaMnO4

[MissPhosgene]

Why not use TEMPO/bleach? Or BaMnO4

All on my list to try.

I want to try the IBX reaction first because it looked a little tricky and therefore might be a good way to improve my skill level.

[discodermolide]

Why not use TEMPO/bleach? Or BaMnO4

All on my list to try.

I want to try the IBX reaction first because it looked a little tricky and therefore might be a good way to improve my skill level.

IBX is not a safe reagent, in industry we won't use it, either TEMPO/Bleach of diacetoxybenzene diacetate/Tempo

[dunno260]

My understanding is that IBX isn't safe (shock sensitive) when its made using potassium bromate, but if you use oxone its fine.  That said, a couple of my group members have made it using potassium bromate on a ~20g scale several times in the process of making Dess-Martin periodinane with no problems.

That said, I would be tempted to try a TEMPO first due to its ease and low cost. 

[MissPhosgene]

I picked IBX because I have some left over from something else.

Votes are with TEMPO, I'll let you know how that goes.

[AC Prabakar]

Hope this may be helpful...

Organic Syntheses, Coll. Vol. 10, p.696 (2004); Vol. 77, p.141 (2000)

If u already encountered this literature ignore my msg.

[ardbeg]

IBX is really easy to make from oxone. 

PCC is an easy reaction as well although sometimes getting rid of the Cr ions can be annoying.

Everyone in my lab swears by schwern though.