Author Topic: can't reduce to save my life......  (Read 511 times)

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amine

  • Guest
can't reduce to save my life......
« on: December 10, 2003, 11:12:00 PM »
Swims' reduction woe's.

Swim tried twice to reduce 2,5-dimethoxynitrostyrene, the first with the Zn+Hcl method which swim had limited success, Swim's assuming swim got .1g of salted material

the second was via the NaBH4 followed by Formic Acid + Zn reduction, this failed horribly. :(

Is there any tips you can give a bee who is serverly challenged when it comes to reducing nitrostyrenes, :(

Swim doesn't want to give up his chemistry endevours, but alas such failures are disappointing.


Q: is the reductive amination via Al/Hg + CH3-N-H2 easier than the reductions for nitrostyrenes?


ah well, swim is going to study for his O-chem test, which make O-chem seem soo much easier in theory.....

Bandil

  • Guest
On the NaBH4 Zn,formic acid reduction you...
« Reply #1 on: December 11, 2003, 01:14:00 AM »
On the NaBH4 Zn,formic acid reduction you might want to post a few more details than you included in your post in order for other people to give advice...

So describe away... Did the BH4 reduction work out, did you isolate the nitroalkane etcetc.? Help your self by asking the questions the smart way  :)

Regards
Bandil


starlight

  • Guest
probably purity issues
« Reply #2 on: December 12, 2003, 09:38:00 AM »
It is easy to get horrific yields from these reactions if you take shortcuts.

Recrystallize your nitrostyrene at least once.

Distill your nitroalkane if you can.

Make sure that you are making your post BH4 workup acidic enough to liberate the nitroalkane, but not too acidic to trigger a nef reaction.

Reductive aminations are easier IME.

amine

  • Guest
ah thx.
« Reply #3 on: December 12, 2003, 04:50:00 PM »