Surf Wiki
Save to docs
general/cycloalkanones

From Surf Wiki (app.surf) — the open knowledge base

Cycloheptanone

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.

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: :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.

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.

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

Uses and reactions

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

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.

References

References

  1. ''[[The Merck Index]]'', 11th Edition, '''2728'''
  2. [http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=C99000|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Cycloheptanone] at [[Sigma-Aldrich]]
  3. Thorpe, T. E.. (1912). "A Dictionary of Applied Chemistry".
  4. Siegel, H.. "Ketones".
  5. Dauben, H. J. Jr.. (1954). "Cycloheptanone".
  6. Cornils, B.. "Dicarboxylic Acids, Aliphatic".
  7. "Dicarboxylic Acids". cyberlipids.org.
  8. (1975). "Reduction of cycloalkanones by several microorganisms". Zeitschrift für Allgemeine Mikrobiologie.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

cycloalkanones seven-membered-rings
Want to explore this topic further?

Ask Mako anything about Cycloheptanone — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report