Oxidation of Benzyl Alcohol with Dilute Nitric Acid

[Stretcher5335]

Just looking to see if anyone has real lab time spent on this reaction. Seems one of the more straight forward and reagent speaking accessible routes to obtain benzaldehyde with good yields. BnOH+HNO3+NaNO2

 

[BrownRiceSyrup]

dude.... wow... thats a damn good article.. thanks for finding that...

I have not done this yet, i did just spend the weekend making it with the sulfuric acid oxidation of BzOH in DMSO route.... via reflux... only an hours worth of refluxing but good god the DMSO thermally decomposes and you are left with a stink that is hard to shake. I mean god awful. They say reflux but dont... i guess my point is, i chose the alternative and im kind of regretting i did, i would have rather liked to have gone by this route... Because my crude benzaldehyde smells like whatever sulfur decomposition product you get, and its awful.... Even after extraction and washing.... Right now its got activated charcoal in it.. maybe i fucked up somewhere but oh well, I imagine either way you'll have to distill and so what.... With the sulfur route the boil is only 1 hour and so thats kind of why i chose it, with close to 95% yield, but i didnt get anywhere near that...

With this method ive seen that it is discolored at the end of the run and you still need to distill it. But at least its just benzaldehyde with maybe some unreacted alcohol... Im pretty confident this route is superior. especially with that article covering the details...

 

[Stretcher5335]

Ive investigated many routes and this is looking to be the leader of them all. You can also use bleach (sodium hypochlorite) to oxidize benzal alc.