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Topic: propargyl alcohol can't be oxidized?  (Read 2510 times)

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Offline ecnerwalc3321

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propargyl alcohol can't be oxidized?
« on: May 08, 2013, 12:49:16 AM »
Hi,

I have some propargyl alcohol that I wish to oxidize into a carboxylic acid.  I am aware that most oxidants also will react with the triple bond.  I've tried putting CrO3 and KCr2O7 into the alcohol directly and even Jones reagent in various concentrations but found that there is no carbonyl peak when I look at the IR.  I was wondering whether these alcohols can't be oxidized for some reason? 


Offline Adamcp898

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Re: propargyl alcohol can't be oxidized?
« Reply #1 on: May 08, 2013, 06:55:30 AM »
If you search for it done using t-Bu hydroperoxide with CuCl as the catalyst I think it has been published. Other than that, I don't think propiolic acid is all that expensive to buy if it's not imperative that you synthesise the stuff

Offline ecnerwalc3321

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Re: propargyl alcohol can't be oxidized?
« Reply #2 on: May 08, 2013, 03:20:34 PM »
I was wondering whether there was an explanation as to why it can or can't be done.  Maybe it has something to do with the allylic position that the alcohol is on?  Would the alcohol be considered a primary alcohol?  I'm not familiar with the method that you mentioned....

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