Rhodium (Chief Bee)
11-27-01 12:19
No 241215
      Phenylacetonitriles from toluenes  Bookmark   

In US Pat 3,002,836 they react o-nitrotoluene with diethyl oxalate to form ethyl-o-nitrophenylpyruvate, which is reacted with hydroxylamine followed by H2SO4 to form o-nitrophenylacetonitrile.

This sounds like a great way to phenylacetonitriles, but they do not give any details on how to do it, and I do not know if the nitro group has anything to do with the reaction. Is there anyone who knows more about this reaction, and possibly have any useful references?
11-27-01 16:48
No 241255
      Re: Phenylacetonitriles from toluenes  Bookmark   

Nitro group (or another strong electron withdrawing group) is required, it makes Me protons acidic enough to allow condensation proceed. Approximate procedure for this condensation


of course there is nothing about further reaction with hydroxylamine and dehydration to nitrile. Anyway this will not work, if there will not be electon withdrawing group on benzene ring.
(Hive Bee)
11-28-01 02:00
No 241413
      Re: Phenylacetonitriles from toluenes  Bookmark   

would multiple methoxy's work?
(Chief Bee)
11-28-01 02:34
No 241425
      Re: Phenylacetonitriles from toluenes  Bookmark   

They are electron donating, so I guess that would make the reaction even more unlikely than without the nitro.
(Hive Bee)
11-28-01 03:16
No 241436
      Re: Phenylacetonitriles from toluenes  Bookmark   

oops, got electron affinity mixed up in that question