[CH2:1]([CH:4]1[CH2:9][CH2:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)(O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:1]([C:4]1[CH2:9][CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH2:6][CH:5]=1)[CH2:2][CH3:3]The compound (18) (13.5 g), p-toluenesulfonic acid (0.4 g) and toluene (250 ml) were mixed, and the mixture was heated under reflux for 2 hours while water being distilled was removed. The reaction mixture was cooled to 30° C., and then water (300 ml) and toluene (500 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solution obtained was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder and dried, giving 7.7 g of 4-propyl-1-(3-fluorophenyl)-3-cyclohexene (19). The yield based on the compound (18) was 61.7%.
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