The formation of bisulfite adducts from aldehydes and ketones is a reaction that has been known for a very long time. The use of this reaction in purifications using aqueous extraction has now been realized by employing a one-phase reaction medium followed by a two-phase separation. The result is a facile and rapid purification technique that allows for separation of aldehydes and unhindered and uncunjugated ketones from mixtures with other organic compounds. This method is highly selective, with removal rates over 95% in almost all cases examined. The recovery of the organic component is also above 95% in nearly all scenarios tested. The bisulfite reaction is also reversible, allowing for re-isolation of the reactive aldehyde or ketone from the aqueous layer. Use of sodium carbonate in this reversion reaction allows for re-isolation of enolizable alpha-chiral aldehydes without loss of optical purity.

Purification of mixtures using bisulfite: Facile separation of aldehydes and ketones through reversible bisulfite adduct formation

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.