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20.2.1.3.1.10 Method 10: Oxidation Using Sodium Chlorite or Sodium Hypochlorite

DOI: 10.1055/sos-SD-020-00065

Lin, S.; Yan, L.; Liu, P.Science of Synthesis, (200720105.

The oxidation of aldehydes to carboxylic acids using sodium chlorite[‌50‌] or sodium hypochlorite,[‌51‌] especially the former, is widely used since a broad range of functional groups survive the reaction conditions. In oxidations with sodium chlorite the addition of 2-methylbut-2-ene,[‌50‌,‌52‌] 2-methylbut-1-ene,[‌53‌] or cyclohexene[‌54‌] is required, as an acid scavenger, in combination with sodium orthophosphate buffered aqueous tert-butyl alcohol as the solvent system. Other solvents, for example, methanol, can also be used.[‌54‌] The conditions employed for the oxidations of the aldehydes 39, 41, 43, and 45 to the appropriate acids 40, 42, 44, and 46 with sodium chlorite or sodium hypochlorite are summarized in Scheme 15.[‌50‌‌54‌]

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