The general procedure for the synthesis of (9Z,12Z)-octadeca-9,12-dien-1-ol from linoleic acid was as follows: lithium aluminum hydride (2.73 g, 72 mmol) was suspended in tetrahydrofuran (THF, 190 mL) cooled to 4 °C. Under stirring, linoleic acid (10 g, 36 mmol) was slowly added dropwise to the above suspension, and stirring was continued for 10 min after completion of the dropwise addition. Subsequently, the reaction mixture was placed in an oil bath and heated to reflux overnight. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by slow addition of 1 mol/L aqueous sodium hydroxide solution (100 mL). The reaction mixture was diluted with ethyl acetate (100 mL) and filtered to remove insoluble material. The filtrate was washed with saturated aqueous sodium bicarbonate, and the organic layer was separated and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by rotary evaporator to obtain the crude product. The crude product was purified by silica gel column chromatography using a continuous gradient of hexane with ethyl acetate as eluent to afford (9Z,12Z)-octadeca-9,12-dien-1-ol (8.68 g, 32.6 mmol) as a colorless oil in 91% yield. The structure of the product was confirmed by proton nuclear magnetic resonance (1H NMR, 500 MHz) with the following chemical shifts: 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).
