7917. Pseudoionone

Nomenclature

CAS number: 141-10-6
6,10-Dimethyl-3,5,9-undecatriene-2-one; citrylideneacetone; 2,6-dimethylhendeca-2,6,8-trien-10-one.
C13H20O; mol wt 192.30.
C 81.20%, H 10.48%, O 8.32%.

Description and references

Intermediate in the synthesis of α- and β-ionone. Prepn from citral and acetone: Tiemann, Krüger, Ber. 26, 2692 (1893); Stiehl, J. Prakt. Chem. [2] 58, 84 (1898); Tiemann, Ber. 32, 115 (1899); Hibbert, Cannon, J. Am. Chem. Soc. 46, 119 (1924); A. Russel, R. L. Kenyon, Org. Synth. coll. vol. III, 747 (1955). A less pure product is obtained by the treatment of oil of lemon grass and acetone with bleaching powder, cobalt nitrate, and alcohol: Ziegler, J. Prakt. Chem. [2] 57, 493 (1898); Tiemann, Ber. 31, 2313 (1898); Haarmann, Reimer & Co., DE 73089; Frdl. 3, 889. Synthesis: T. Onishi et al., Synthesis 1980, 651.

Chemical structure

Properties

Pale yellow oil, bp2 114-116°; bp4 124-126°; bp12 143-145°; d20 0.8984; nD20 1.53346.