[CH2:1]([C:6]1[CH2:11][CH2:10][CH:9]([C:12](O)=[O:13])[CH2:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Li].[H-].Cl>O1CCCC1.O>[CH2:1]([C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]A solution of 4-pentyl-3-cyclohexen-l-carboxylic acid (3.4 g) in tetrahydrofurn (THF; 55 ml) was added dropwise to a cold (0° C.) solution of lithium aluminim hydride (1.37 g) in tetrahydrofuran (THF, 55 ml), in a flask equipped with a condenser. The reaction mixture was stirred at room temperature for at least three hours, re-cooled to 0° C., and water (8 ml) was then added dropwise. An additional 55 ml of THF was added, and the reaction mixture stirred for three hours. The reaction mixture was then acidified with 2 M HCl (150 ml), and extracted with a 1:1 (v:v) ethyl acetate:hexane mixture. The combined organic layers were extracted with saturated sodium chloride and dried over sodium sulfate. The solvent was removed in vacuo, and the resultant oil was distilled (92°-95° C. at c.a. 1 mm Hg) to produce 4-pentyl-3-cyclohexen-1-methanol.
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