Trouble with saponification.
I'm trying to saponify this product, the di-methyl-azido-mesaconate ester:
However, upon addition of a 5% NaOH solution - I get extensive gas formation (N2) and my analysis shows that a di-acid is formed, however in yields
that are less than pleasant.
It seems that this compound is very fragile in polar media, but I cannot - for the life of me - figure out what is happening upon addition of OH- that
would cause N2 to be given off.
I tried to look up mechanisms, but they are limited and I couldn't quite relate them. - if you guys want a head start with this problem look up
curtius rearangements. . .
Any thoughts would be appreciated.
Next time I try the saponification I am going to dilute the product in ether, and add the molar equivalents of OH- in around a 2% solution and just
let it go for an extra day or so :\ . . .
[Edited on 5-4-2011 by GreenD]
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