Cyclopentanone Explained

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

Preparation

Upon treatment with barium hydroxide at elevated temperatures, adipic acid undergoes ketonization to give cyclopentanone:[1]

(CH2)4(CO2H)2 → (CH2)4CO + H2O + CO2

Uses

Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.[2] It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.[3]

Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.[3]

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 octonitrocubane.[4]

Notes and References

  1. .
  2. Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.
  3. Encyclopedia: Hardo Siegel . Manfred Eggersdorfer . Ketones . Ullmann's Encyclopedia of Industrial Chemistry. 2005. Wiley-VCH. Weinheim. 10.1002/14356007.a15_077. 978-3-527-30673-2 .
  4. Bliese . Marianne . Tsanaktsidis . John . 1997 . Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis . Australian Journal of Chemistry . en . 50 . 3 . 189 . 10.1071/C97021 . 0004-9425.

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