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Cycloheptanone
Chemical compound

Cycloheptanone, (CH2)6CO, is a cyclic ketone also referred to as suberone. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals.

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Synthesis

In 1836, French chemist Jean-Baptiste Boussingault first synthesized cycloheptanone from the calcium salt of dibasic suberic acid. The ketonization of calcium suberate yields calcium carbonate and suberone:1

Ca(O2C(CH2)6CO2) → CaCO3 + (CH2)6CO

Cycloheptanone is still produced by the cyclization and decarboxylation of suberic acid or suberic acid esters. This reaction is typically conducted in the gas phase at 400–450 °C over alumina doped with zinc oxide or cerium oxide.2

Cycloheptanone is also produced by the reaction of cyclohexanone with sodium ethoxide and nitromethane. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to acetic acid and shaken with hydrogen gas in the presence of W-4 Raney nickel catalyst. Sodium nitrite and acetic acid are then added to give cycloheptanone.3

Cycloheptanone is also prepared by ring expansion of cyclohexanone with diazomethane as the methylene source.4

Uses and reactions

Cycloheptanone is a precursor to bencyclane, a spasmolytic agent and vasodilator.5 Pimelic acid is produced by the oxidative cleavage of cycloheptanone.6 Dicarboxylic acids such as pimelic acid are useful for the preparation of fragrances and certain polymers.7

Several microorganisms, including Mucor plumbeus, Mucor racemosus, and Penicillium chrysogenum, have been found to reduce cycloheptanone to cycloheptanol. These microorganisms have been investigated for use in certain stereospecific enzymatic reactions.8

References

  1. Thorpe, T. E. (1912). A Dictionary of Applied Chemistry. LCCN 12009914. /wiki/LCCN_(identifier) ↩

  2. Siegel, H.; Eggersdorfer, M. "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 ↩

  3. Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19; Collected Volumes, vol. 4, p. 221. http://www.orgsyn.org/demo.aspx?prep=cv4p0221 ↩

  4. Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19; Collected Volumes, vol. 4, p. 221. http://www.orgsyn.org/demo.aspx?prep=cv4p0221 ↩

  5. Siegel, H.; Eggersdorfer, M. "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 ↩

  6. Cornils, B.; Lappe, P. "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.pub2. ISBN 978-3-527-30673-2. 978-3-527-30673-2 ↩

  7. "Dicarboxylic Acids". cyberlipids.org. Archived from the original on 2011-09-07. Retrieved 2011-04-26. https://web.archive.org/web/20110907093548/http://www.cyberlipid.org/fa/acid0004.htm ↩

  8. Lemiere, G. L.; Alderweireldt, F. C.; Voets, J. P. (1975). "Reduction of cycloalkanones by several microorganisms". Zeitschrift für Allgemeine Mikrobiologie. 15 (2): 89–92. doi:10.1002/jobm.19750150204. /wiki/Doi_(identifier) ↩