ChemicalBook CAS DataBase List Guaiazulene

Guaiazulene synthesis

4synthesis methods

Product Name:Guaiazulene
CAS Number:489-84-9
Molecular formula:C15H18
Molecular Weight:198.3

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.

Ethanamine, 2,2'-[[2-[3,8-dimethyl-5-(1-methylethyl)-1-azulenyl]ethenylidene]bis(4,1-phenyleneoxy)]bis[N,N-dimethyl-

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275-51-4 Synthesis

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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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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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275-51-4 Synthesis

275-51-4
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$50.00/100 mg

489-84-9
297 suppliers
$29.00/5mg

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References

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13061-96-6
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489-84-9
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$29.00/5mg

References

1000210-73-0
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489-84-9
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$29.00/5mg

References

Guaiazulene Related Search:

Dimethyl ether Isopropyl alcohol Diisopropylamine Dimethyl sulfoxide Guaiacol Dimethyl sebacate Dimethyl carbonate N-Methyl-2-pyrrolidone N,N-Diisopropylethylamine Guaifenesin