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Aldol

1=Organic compound of the form R–CH(OH)–CHR–C(=O)–R

Aldol

1=Organic compound of the form R–CH(OH)–CHR–C(=O)–R

General aldol structure showing the α and 𝛽 positions of carbons relative to the carbonyl. When R" is -H, it is an aldol, when R" is a carbon, it is a ketol.

In organic chemistry, an aldol is a structure consisting of a hydroxy group (-OH) two carbons away from either an aldehyde or a ketone. The name combines the suffix 'ol' from the alcohol and the prefix depending on the carbonyl group, either 'ald' for an aldehyde, or 'ket' for a ketone, in which case it referred to as a 'ketol'. An aldol may also use the term β-hydroxy aldehyde (or β-hydroxy ketone for a ketol). The term "aldol" may refer to 3-hydroxybutanal.

Aldols are the product of a carbon-carbon bond-formation reaction, giving them wide applicability as a precursor for a variety of other compounds.

Synthesis and reactions

Aldols are usually synthesized from an aldol addition reaction using two aldehydes or an aldehyde and a ketone for a ketol. These reactions may also be done intramolecularly to form 5 or 6 member rings or for stereoselective syntheses in the active area of asymmetric synthesis.

Aldols may also undergo a condensation reaction in which the hydroxy group is replaced by a pi bond. The final structure is a reactive α,β-unsaturated carbonyl compound, which can also be used in a variety of other reactions: :RC(O)CH2CH(OH)R' → RC(O)CH=CHR' + H2O

Applications

Aldols synthesized from two aldehydes are usually unstable, often producing secondary compounds such as diols, unsaturated aldehydes, or alcohols. Hydroxypivaldehyde is a rare example of a distillable aldol. The aldol 3-hydroxybutanal is a precursor to quinaldine, which is a precursor to the dye quinoline Yellow SS.

Aldols are also used as intermediates in the synthesis of polyketide natural products and drugs such as Oseltamivir and Epothilone.

References

References

  1. (15 January 2013). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry.
  2. PubChem. "CID 21282929".
  3. (21 May 2018). "Robust Bulky [P,O] Neutral Nickel Catalysts for Copolymerization of Ethylene with Polar Vinyl Monomers". ACS Catal..
  4. (2006). "Modern aldol methods for the total synthesis of polyketides". Angewandte Chemie International Edition.
  5. (2009). "Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions". Synthesis.
  6. (15 October 2010). "A synthesis of oseltamivir (Tamiflu) starting from D-mannitol". J Org Chem.
  7. Schinzer, Dieter. (2004-06-24). "The Aldol Reaction in Natural Product Synthesis: The Epothilone Story". Wiley.
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