Phorone

Preparation

It was first obtained in 1837 in impure form by the French chemist Auguste Laurent, who called it "camphoryle". In 1849, the French chemist Charles Frédéric Gerhardt and his student Jean Pierre Liès-Bodart prepared it in a pure state and named it "phorone".See:

• Gerhardt, Charles (1849) Comptes rendus des travaux de chimie (Paris, France: Masson, 1849), p. 385. (in French)
• From p. 293: "Dieses Oel, welches Gerhardt und Lies-Bodart mit dem Namen Phoron bezeichnen, … " (This oil, which Gerhardt and Liès-Bodart designate by the name "phorone", … ) On both occasions it was produced by ketonization through the dry distillation of the calcium salt of camphoric acid.

:

It is now typically obtained by the acid-catalysed twofold aldol condensation of three molecules of acetone. Mesityl oxide is obtained as an intermediate and can be isolated.

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

Reactions

Phorone can condense with ammonia to form triacetone amine.

References

• Merck Index, 11th Edition, 7307.

References

1. (1837). "Sur les acides pinique et sylvique, et sur le camphoryle". Annales de Chimie et de Physique.
2. Watts, Henry, ''A Dictionary of Chemistry and the Allied Branches of Other Sciences'' (London, England: Longmans, Green, and Co., 1863), vol. 1, "Camphorone", [https://babel.hathitrust.org/cgi/pt?id=nyp.33433079412726;view=1up;seq=753 p. 733.]
3. (1866). "Lehrbuch der organischen Chemie". Ferdinand Enke.
4. Hardo Siegel. (2005). "Ketones". Wiley-VCH.