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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: zsinger on November 19, 2013, 08:09:47 PM

Title: Wacker Oxidation Advice
Post by: zsinger on November 19, 2013, 08:09:47 PM
All,
About to perform a wacker oxidation, and I decided to use P-Benzoquinone instead of CuCl2 as my oxidant this time .  I have only performed this reaction once in the lab, as it is almost always scaled up.  I prefer the Formic Acid/H2O2 with 5M H2SO4 workup to get the desired ketone (stick with what you know!), but I wanted to practice this method, as oxygen is cheap, and P-Benzo is not all that expensive!  Thanks for any/all help.  The Rxn. hopefully should proceed as follows (balanced):   2 Ethylene, add PdCl2, Add p-benzoquinone-->2 CH3COH.
      -Zack
Title: Re: Wacker Oxidation Advice
Post by: Archer on November 20, 2013, 04:47:19 AM
What are you attempting to oxidise? by the looks of your post you are attempting to make acetaldehyde from ethene.
Title: Re: Wacker Oxidation Advice
Post by: zsinger on November 20, 2013, 12:35:07 PM
I am trying this on the terminal end of Eugenol to get the desired ketone.  I just posted the acetaldehyde expression to explain my additions, etc. Thanks
      -Z
Title: Re: Wacker Oxidation Advice
Post by: AlphaScent on November 20, 2013, 01:19:06 PM
Eugenol huh.  Then what, safrole??

I am suspicious about this post.
Title: Re: Wacker Oxidation Advice
Post by: Archer on November 20, 2013, 01:33:39 PM
I am trying this on the terminal end of Eugenol to get the desired ketone.  I just posted the acetaldehyde expression to explain my additions, etc. Thanks
      -Z

Wacker oxidation does not give the ring substituted 1-arylpropan-2-one with eugenol.

See http://www.sciencedirect.com/science/article/pii/S0040403901803026 for details.


Title: Re: Wacker Oxidation Advice
Post by: zsinger on November 20, 2013, 01:42:27 PM
Anyways, ill figure it out I guess.
Title: Re: Wacker Oxidation Advice
Post by: zsinger on November 20, 2013, 03:15:38 PM
Retracted statement.
Title: Re: Wacker Oxidation Advice
Post by: Archer on November 20, 2013, 03:40:56 PM
Also, If you know of a way to go from Eugenol to Safrole without adding HI and disrupting that double bond, you would be a rich man (or woman).

I am not familiar with US law but certainly in many parts of the world if you succeeded in synthesising safrole by any route you would be committing a very serious offence.

Many roads lead to Rome, in this case fortune is not found there.

Probably something to avoid discussing on this forum.