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ChemicalBook CAS DataBase List Guaiazulene
489-84-9

Guaiazulene synthesis

4synthesis methods
Guaiazulene is a dark blue crystalline hydrocarbon,it is synthesised by 2,2'-[[2-[3,8-dimethyl-5-(1-methylethyl)-1-azulenyl]ethenylidene]bis(4,1-phenyleneoxy)]bis[N,N-dimethyl-Ethanamine and AZULENE,with hydrogenchloride in methanol;water;acetonitrile at 60.
-

Yield: 97% ， 58%

Reaction Conditions:

with hydrogenchloride in methanol;water;acetonitrile at 60; for 3 h;

Steps:

4.1.10. Reaction of 1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}-2-(3-guaiazulenyl)ethylene (13) with azulene (1)
To a solution of a commercially available 1 (5 mg, 39 μmol) in methanol (2 mL) was added a solution of 13 (20 mg, 36 μmol) in acetonitrile (3 mL). The mixture containing 36% hydrochloric acid (50 μL) was stirred at 60 °C for 3 h. After the reaction, distilled-water was added to the mixture and then the resulting products were extracted with dichloromethane (10 mL×3). The extract was washed with distilled-water, dried (MgSO4), and evaporated in vacuo. The residue thus obtained was carefully separated by silica gel column chromatography with methanol-dichloromethane (30:70, v/v) as an eluant. Guaiazulene1 (10) (7 mg, 35 μmol, 97% yield) and a new compound 2-(azulen-1-yl)-1,1-bis{4-[2-(dimethylamino)ethoxy]phenyl}ethylene (18) (10 mg, 21 μmol, 58% yield) were isolated. The structure of the product 10 was identified on the basis of silica gel TLC analysis and EIMS and 1H NMR spectral data. Along with the above products, this reaction gave a chromatographically inseparable mixture of dark brown-colored polar resinous substances.

References:

Takekuma, Shin-Ichi;Kaibara, Masamichi;Minematsu, Toshie;Takekuma, Hideko [Tetrahedron,2011,vol. 67,# 26,p. 4780 - 4792] Location in patent:experimental part

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