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Cyclopentanone

Cyclopentanone

Adipic ketone 2-pentanone 3-pentanone cyclopentenone

Cyclopentanone is the organic compound with the formula (CH2)4CO. This cyclic ketone is a colorless volatile liquid.

Preparation

Ketonic decarboxylation of adipic acid gives cyclopentanone. The reaction is conducted at elevated temperatures in the presence of barium hydroxide. :[[File:Barium adipate pyrolysis.png|frameless|400px]]

The Pd-catalyzed oxidation of cyclopentene also gives cyclopentanone.

Uses

Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone. It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.

Cyclopentobarbital, a drug made from cyclopentanone

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.

It is also used as a precursor to cubane-1,4-dicarboxylate, which is used to synthesize other substituted cubanes, such as the high explosives heptanitrocubane and octanitrocubane.

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''2748'''.
  2. {{Sigma-Aldrich. sial
  3. (1925). "Cyclopentanone". Org. Synth..
  4. (2016). "Ullmann's Encyclopedia of Industrial Chemistry".
  5. Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.{{doi. 10.1002/14356007.t11_t01
  6. Hardo Siegel. (2005). "Ketones". Wiley-VCH.
  7. (1997). "Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis". Australian Journal of Chemistry.
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cycloalkanones ketone-solvents perfume-ingredients cyclopentanes
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