ChemicalBook CAS DataBase List CIS,CIS-9,12-OCTADECADIENOL

CIS,CIS-9,12-OCTADECADIENOL synthesis

6synthesis methods

Product Name:CIS,CIS-9,12-OCTADECADIENOL
CAS Number:506-43-4
Molecular formula:C18H34O
Molecular Weight:266.46

60-33-3 Synthesis

60-33-3
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$9.00/5g

506-43-4
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$13.00/100mg

Yield:506-43-4 91%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuranReflux;

Steps:

1.1 (9z,12z)-Octadecadien-1-ol
Lithium aluminum hydride (2.73 g, 72 mmol) was suspended in tetrahydrofuran (THF, 190 mL) cooled at 4° C. Linoleic acid (10 g, 36 mmol) was added dropwise to the suspension, and the resulting mixture was stirred for 10 minutes. Then, the mixture was refluxed overnight with heating on an oil bath. After cooling the mixture, 1 mol/L aqueous sodium hydroxide (100 mL) was added to terminate the reaction. Then, the reaction mixture was diluted with ethyl acetate (100 mL), and filtered, and the filtrate was washed with saturated aqueous sodium hydrogencarbonate. Then, the organic layer was collected, and dried over anhydrous sodium sulfate. The organic layer was filtered, and the solvent was evaporated by using a rotating evaporator to obtain a crude product. The crude product was purified by silica gel chromatography (elution solvent, hexane:ethyl acetate, continuous gradient) to obtain 9z,12z-octadecadien-1-ol (8.68 g, 32.6 mmol) as colorless oil. Yield was 91%. Proton nuclear magnetic resonance (¹H NMR, 500 MHz) data of 9z,12z-octadecadien-1-ol δ=0.88 (t, 3H), 1.25-1.36 (m, 16H), 1.53-1.58 (m, 2H), 2.02-2.06 (m, 4H), 2.76 (t, 2H), 3.62 (t, 2H), 5.29-5.40 (m, 4H)

References:

NATIONAL UNIVERSITY CORPORATION HOKKAIDO UNIVERSITY;Harashima, Hideyoshi;Sato, Yusuke;Warashina, Shota;Hatakeyama, Hiroto;Hyodo, Mamoru;Nakamura, Takashi US2017/273905, 2017, A1 Location in patent:Paragraph 0086-0087

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