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I was thinking about using 2-Iodoxybenzoic acid to selectively oxidize primary alcohols to aldehydes. I've found papers using various solvents like acetone/water mixture1, 2-methyl-2-propanol2, DMSO or bromobenzene3.

My question are:

  1. How to choose the most suitable solvent for an IBX reaction?

  2. IBX reduces to iodosobenzoic acid which can be filtered out together with leftover IBX and oxidized back to IBX using Oxone and reused. After filtering the reaction mixture and distilling the solvent, we get reasonably pure aldehyde for further use.

    Is this workup procedure correct?

  3. Could be IBX prepared in situ from 2-iodobenzoic acid and potassium persulfate?

References:

  1. Mild Oxidation of Alcohols with o-Iodoxybenzoic Acid (IBX) in Water/Acetone Mixture in the Presence of β-Cyclodextrin, K. Surendra, N. Srilakshmi Krishnaveni, M. Arjun Reddy, Y. V. D. Nageswar, and K. Rama Rao The Journal of Organic Chemistry 2003 68 (5), 2058-2059 DOI: 10.1021/jo026751w

  2. Scott A. Van Arman, 2-Methyl-2-propanol as solvent for o-iodoxybenzoic acid (IBX) oxidation of 1˚ alcohols to aldehydes, Tetrahedron Letters, Volume 50, Issue 33, 2009, DOI: 10.1016/j.tetlet.2009.06.045.

  3. Iodine(V) Reagents in Organic Synthesis. Part 4. o-Iodoxybenzoic Acid as a Chemospecific Tool for Single Electron Transfer-Based Oxidation Processes, Nicolaou et.al, J. AM. CHEM. SOC. 9 VOL. 124, NO. 10, 2002, DOI: 10.1021/ja012127

  4. A Simple and Advantageous Protocol for the Oxidation of Alcohols with o-Iodoxybenzoic Acid (IBX), Jesse D. More and Nathaniel S. Finney Organic Letters 2002 4 (17), 3001-3003, DOI: 10.1021/ol026427n

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  • $\begingroup$ @Waylander I'd like to avoid bromates as bromide impurities in the final product increase explosion hazard. I'd like to generate iodoxybenzoic acid in situ using potassium peroxymonosulfate (oxone) but more favourable would be potassium persulfate for me. I'm a bit worried if it could oxidize the starting alcohol to carboxylic acid. $\endgroup$
    – steve d.
    Commented Jul 21, 2021 at 10:52
  • $\begingroup$ I cannot find a ref for persulfate oxidation of 2-Iodobenzoic acid but Potassium persulfate and 3-methylimidazolinium triflate has been used to oxidise alcohols to aldehydes. tandfonline.com/doi/abs/10.1080/… $\endgroup$
    – Waylander
    Commented Jul 21, 2021 at 11:10
  • $\begingroup$ @Waylander I meant for the preparation of IBX, not for actual oxidation. (2-iodobenzoic acid and potassium persulfate) $\endgroup$
    – steve d.
    Commented Jul 21, 2021 at 11:13
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    $\begingroup$ I realised that, hence my comment about not being able to find a reference for IBX prep using potassium persulfate. $\endgroup$
    – Waylander
    Commented Jul 21, 2021 at 11:48

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