Linoleyl alcohol

ChEBI: A long chain fatty alcohol that is octadecanol containing two double bonds located at positions 9 and 12 (the 9Z,12Z-geoisomer).

(9Z,12Z)-octadecadien-1-ol is a long chain fatty alcohol that is octadecanol containing two double bonds located at positions 9 and 12 (the 9Z,12Z-geoisomer). It is a long-chain primary fatty alcohol and a fatty alcohol 18:2.

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 91percent. Proton nuclear magnetic resonance (A 1 L glass reactor fitted with an argon inlet was purged with dry argon, and charged with of linoleic acid (30 g, 107 mmol) and THF (320 mL). The reaction mixture was cooled to 0° C. with acetone-dry-ice mixture. While maintaining the reaction temperature below 0° C., 73 mL of sodium his (2-methoxyethoxy) aluminum hydride solution in methylbenzene (60percent wt/vol) was added drop wise. After the completion of addition, the reaction mixture was incubated at ambient temperature for 2 hours. After reaction, the reaction mixture was cooled to 0° C. To the reaction mixture, a saturated sodium sulfate solution (prepared by dissolving 5.75 g Na30 g of linoleic acid (Reactant 1) and THF (320 ml) were added to the reactor. 73 ml of a red aluminum solution (60percent wt/vol) in toluene was slowly added dropwise to the reactor, keeping the temperature at about 0°C during the addition. After the addition was completed, the reaction was performed at room temperature for 2 hours.The solution was cooled to 0°C and saturated sodium sulfate solution was slowly added.After the addition was completed, 130 ml of ethyl acetate was added dropwise over 30 minutes.Stir vigorously. The reaction solution was filtered and the solid was washed with ethyl acetate. The organic phases were combined and concentrated. The product was dissolved in 80 ml of ethyl acetate, washed twice with water, and dried over anhydrous sodium sulfate. filter, The organic phase was concentrated to remove the solvent to give product 2 (28.8 g).30 g of linoleic acid (Reaction 1) and THF (320 ml) were charged to the reactor. 73 ml of a Sodium bis(2-methoxyethoxy)aluminium hydride (trade name Red-Al) solution (60percent wt/vol) in toluene solution was slowly added dropwise to the reactor, and the temperature was maintained at about 0 ° C during the dropwise addition. After the completion of the dropwise addition, the reaction was carried out for 2 hours at room temperature. The solution was cooled to 0 ° C and a saturated sodium sulfate solution was slowly added. After the dropwise addition was completed, 130 ml of ethyl acetate was added dropwise within 30 minutes, and vigorously stirred. The reaction mixture was filtered, solid was washed with ethyl acetate, and then organic phases were combined and concentrated. The product was dissolved in 80 ml of ethyl acetate, washed twice with water and dried over anhydrous sodium sulfate. Filtration and concentration was carried out for the organic phase to remove solvent, and obtain Intermediate 2 (28.8 g).

Molecular Weight:266.5
XLogP3:6.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:14
Exact Mass:266.260965704
Monoisotopic Mass:266.260965704
Topological Polar Surface Area:20.2
Heavy Atom Count:19
Complexity:206
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes