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