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Related Experiment Videos

4-Ethoxycarbonyl-3-hydroxy-3-phenylcyclohexanone.

S Hernández-Ortega1, F Jiménez-Cruz, H Ríos-Olivares

  • 1Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510 México DF, Mexico. simonho@servidor.unam.mx

Acta Crystallographica. Section C, Crystal Structure Communications
|April 21, 2001
PubMed
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This study details the synthesis of ethyl 2-hydroxy-4-oxo-2-phenylcyclohexanecarboxylate via Michael-Aldol condensation. Structural analysis reveals specific group configurations and intermolecular hydrogen bonding in the crystalline state.

Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Michael-Aldol condensation is a key reaction in organic synthesis.
  • Understanding the stereochemistry and intermolecular interactions of complex organic molecules is crucial.

Purpose of the Study:

  • To synthesize and characterize ethyl 2-hydroxy-4-oxo-2-phenylcyclohexanecarboxylate.
  • To elucidate the conformational preferences and intermolecular hydrogen bonding of the title compound in the solid state.

Main Methods:

  • Michael-Aldol condensation reaction.
  • Single-crystal X-ray diffraction analysis.

Main Results:

  • The synthesis yielded the target compound, ethyl 2-hydroxy-4-oxo-2-phenylcyclohexanecarboxylate.
  • The cyclohexanone ring adopted a chair conformation.

Related Experiment Videos

  • Specific stereochemical configurations were determined: beta-axial for the hydroxyl group, beta-equatorial for the ethoxycarbonyl group, and alpha-equatorial for the phenyl group.
  • An intermolecular hydrogen bond between the hydroxyl group and the ring carbonyl was observed (O...O distance of 2.874 Å).
  • Additional weak intermolecular hydrogen bonds (C-H...O and O-H...O) were identified.

    • Conclusions:

    • The study successfully synthesized and characterized a complex cyclohexanecarboxylate derivative.
    • The findings provide insights into the conformational behavior and intermolecular interactions governing the crystal packing of this molecule.