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Topic: Yield improvement on vanillin reduction?  (Read 3507 times)

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Offline Amndz

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Yield improvement on vanillin reduction?
« on: October 23, 2011, 10:26:41 PM »
How can the yield of a vanillin reduction lab be improved?
In my lab about .4g NaBH4 was added to a chilled solution of 3g vanillin and 22mL NaOH, and about 10mL of 3M HCl was added in workup. I got a 72% yield, but I'm not sure how that could be improved.. How should I approach coming up with this?

 Thanks in advance!

Offline orgopete

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Re: Yield improvement on vanillin reduction?
« Reply #1 on: October 24, 2011, 08:11:12 AM »
Check the stoichiometry.
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Offline Honclbrif

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Re: Yield improvement on vanillin reduction?
« Reply #2 on: October 24, 2011, 08:53:32 AM »
Was your product contaminated with unreacted starting material, or was it relatively pure but you just lost material along the way?
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Offline orgopete

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Re: Yield improvement on vanillin reduction?
« Reply #3 on: October 25, 2011, 08:19:29 AM »
I was looking at this from an atom efficiency point of view. I am presuming the reaction went to completion.

If you wish to improve the material balance, you could simply extract your alcohol from the reaction mixture. Semantically, that will improve your recovery. The yield can also be thought of as a function of the reaction.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

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