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.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.4
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.5
References
Thorpe, J. F.; Kon, G. A. R. (1925). "Cyclopentanone". Org. Synth. 5: 37. doi:10.15227/orgsyn.005.0037. /wiki/Doi_(identifier) ↩
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 /wiki/Doi_(identifier) ↩
Hardo Siegel; Manfred Eggersdorfer (2005). "Ketones". Ketones. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩
Hardo Siegel; Manfred Eggersdorfer (2005). "Ketones". Ketones. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩
Bliese, Marianne; Tsanaktsidis, John (1997). "Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis". Australian Journal of Chemistry. 50 (3): 189. doi:10.1071/C97021. ISSN 0004-9425. http://www.publish.csiro.au/?paper=C97021 ↩