Cyclopentanone

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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]

File:Barium adipate pyrolysis.png

The Pd-catalyzed oxidation of cyclopentene also gives cyclopentanone.[2]

Uses

Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.[3] It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.[4]

File:Cyclopal.svg
Cyclopentobarbital, a drug made from cyclopentanone

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

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