Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a

geranium ''Geranium'' is a genus of 422 species of annual, biennial, and perennial plants that are commonly known as geraniums or cranesbills. They are found throughout the temperate regions of the world and the mountains of the tropics, with the gre ...

odor, with

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

or .

Preparation

It was first obtained in 1837 in impure form by the French chemist

Auguste Laurent Auguste Laurent (14 November 1807 – 15 April 1853) was a French chemist who helped in the founding of organic chemistry with his discoveries of trichloroethylene, anthracene, phthalic acid, and carbolic acid. He devised a systematic nomenc ...

, who called it "camphoryle". In 1849, the French chemist

Charles Frédéric Gerhardt Charles Frédéric Gerhardt (21 August 1816 – 19 August 1856) was a French chemist, born in Alsace and active in Paris, Montpellier, and his native Strasbourg. Biography He was born in Strasbourg, which is where he attended the gymnasium (an ...

and his student Jean Pierre Liès-Bodart prepared it in a pure state and named it "phorone". On both occasions it was produced by

ketonization Ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction involving decarboxylation, converting two equivalents of a carboxylic acid () to a symmetric ketone (). The reaction typically requires heat and a ...

through the dry distillation of the calcium salt of camphoric acid. : It is now typically obtained by the acid-catalysed twofold

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...

of three molecules of

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

. Mesityl oxide is obtained as an intermediate and can be isolated. Phoron formation

Crude phorone can be purified by repeated recrystallization from ethanol or ether, in which it is soluble.

Reactions

Phorone can condense with

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

to form triacetone amine.

References

*''Merck Index'', 11th Edition, 7307. {{reflist

External links

International Chemical Safety Cards
Ketones Alkene derivatives

Preparation

Reactions

See also

References

External links