plasticperson32 - 30-6-2015 at 08:21
Preparation of 2,6-napthalenedinitrile from 2,6-napthalenedicarboxylic acid
-The theoretical synthesis ive been following:
(diacid > diamide > dinitrile)
There has been no problem forming the diamide from heating the diacid with urea/boric acid/diacid and washing the product with water. However, there
is a possibility that there is presence of a half reacted acid/amide.
Subsequently, dehydrating the diamide with Polyphosophoric acid or acetic anhydride has both failed. The IR's show that the diamide is converting back
to the diacid during the dehydration process.
Does anyone know why this is happening and another approach I could use to synthesize the dinitirle.
gdflp - 30-6-2015 at 09:02
Washing the product of the melt with dilute alkali/ammonia solution should increase the solubility of the mixed acid/amide and diacid in water and
thus remove those products. If the dehydration with acetic anhydride isn't working(I'm rather surprised, how long are you relfuxing?), you could
always use a Hofmann rearrangement followed by diazotization of the amine with CuCN to yield the dinitrile.
CuReUS - 1-7-2015 at 06:23
just last night,I read a new reaction called Letts nitrile synthesis of aromatic cyanides using KSCN.
nitriles can also be made in one pot using aromatic carboxylic acid, urea and sulphamic acid
http://www.sciencemadness.org/whisper/viewthread.php?tid=380...
http://chemistry.mdma.ch/hiveboard/novel/000401843.html
[Edited on 1-7-2015 by CuReUS]