Cyclopentanone Explained

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

Preparation

intramolecular ketonization of adipic acid gives cyclopentanone. The reaction is conducted at elevated temperatures in the presence of barium hydroxide.^[1]

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 octanitrocubane.^[4]

Notes and References

1. Org. Synth.. J. F.. Thorpe. G. A. R.. Kon. 1925. Cyclopentanone. 5. 37. 10.15227/orgsyn.005.0037.
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 . 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.