Benzyl chloride from Toluene/trichloroisocyanuric

[acx01b]

Hi,

Preparation of Benzyl Chloride (44% yield?) by refluxing Toluene and trichloroisocyanuric acid, with Benzoyl Peroxide as catalyst looks interesting...

other catalyst known ?

[Organikum]

other catalyst known ?

Yes! There are other catalysts!

regards
ORG

[moo]

It's not a catalyst, it's a radical initiator.

[Nicodem]

There are many radical initiators that can substitute it, practicaly any compound with the -CO-OO-CO- group will do, probably AIBN or other aza compounds would work as well. And quite probably a mercury lamp would suffice too. But as far as I know, peroxybenzoic acid anhydride (aka "benzoyl peroxide") is the only one that you can easily get OTC, so I can see no point in your question. Or are you perhaps interested in other radical initiators that might increase the yields?

[acx01b]

ok ty very much
Does peroxyacetic acid anhydride work ?
can it be formed from H2S2O8 NaOH and acetic acid ?

[psyloxy]

Patent US2439399

Patent US2458207

...dangerous stuff !

--psyloxy--

[acx01b]

what about using 2-acetoxybenzoic acid to obtain di(2-hydroxybenzoyl)peroxide ?

Aspirin + NaOH  --> Na-acetate + 2-hydroxybenzoic acid
(advices for separation?)

[Nicodem]

Besides of being impossible to prevent the self oxydation of such a peroxyde, WHY?

What the hell is wrong with peroxybenzoic anhydride? It is OTC all over the world and it gives acceptable yields, so why do you insist on these ideas? Could you share your secret reasons with us!

[acx01b]

no secret reasons, the reason is that the route throw aspirin to Ph-CH2Cl is funny !


sory i didn't understand your 1st match, you say di(2-hydroxybenzoyl)peroxide won't be obtained ? what will be obtained that way ?

[yei]

sunlight works nicely, apparently.

In a similar benzylic chlorination (with t-butyl peroxide), it was greatly superior to chemical radiacal initiators.