Diol - Synthesis

Synthesis

Because diols are a common functional group arrangement, numerous methods of preparation have been developed.

  • Vicinal diols can be produced from the oxidation of alkenes, usually with dilute acidic potassium permanganate, also known as potassium manganate(VII). Using alkaline potassium manganate(VII) produces a colour change from clear deep purple to clear green; acidic potassium manganate(VII) turns clear colourless.
  • Osmium tetroxide can similarly be used to oxidize alkenes to vicinal diols.
  • Hydrogen peroxide reacts with an alkene to the epoxide and then by saponification to the diol for example in the synthesis of trans-cyclohexanediol batch or by microreactor :
  • A chemical reaction called Sharpless asymmetric dihydroxylation can be used to produce chiral diols from alkenes using an osmate reagent and a chiral catalyst.
  • Another method is the Woodward cis-hydroxylation (cis diol) and the related Prévost reaction (anti diol), depicted below, which both use iodine and the silver salt of a carboxylic acid.
  • In the Prins reaction 1,3-diols can be formed in a reaction between an alkene and formaldehyde.
  • Geminal diols can be formed by the hydration of ketones.

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