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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: ecnerwalc3321 on May 08, 2013, 12:49:16 AM

Title: propargyl alcohol can't be oxidized?
Post by: ecnerwalc3321 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? 

Title: Re: propargyl alcohol can't be oxidized?
Post by: Adamcp898 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

Title: Re: propargyl alcohol can't be oxidized?
Post by: ecnerwalc3321 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....