Reaction SMILES: [CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=3[F:25])[CH2:14][CH:13]=2)=[C:8]([F:26])[C:7]=1[F:27])[CH2:2][CH2:3][CH3:4].C([Li])(CC)C.[F:33][C:34]1[C:39]([F:40])=[C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:37]=[CH:36][C:35]=1[CH:48]1[CH2:53][CH2:52][C:51](=O)[CH2:50][CH2:49]1.[Cl-].[NH4+]>CCCCCC.C1CCCCC1.C1COCC1.C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([C:51]4[CH2:52][CH2:53][CH:48]([C:35]5[CH:36]=[CH:37][C:38]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[C:39]([F:40])[C:34]=5[F:33])[CH2:49][CH:50]=4)=[C:20]([F:24])[C:19]=3[F:25])[CH2:14][CH:13]=2)=[C:8]([F:26])[C:7]=1[F:27])[CH2:2][CH2:3][CH3:4]
Reactant: CCCCOc1ccc(C2=CCC(c3cccc(F)c3F)CC2)c(F)c1F
Reactant: CCCCCCOc1ccc(C2CCC(=O)CC2)c(F)c1F
Agent: [Cl-]
Agent: [Li]C(C)CC
Agent: [NH4+]
Solvent: C1CCCCC1
Solvent: CCCCCC
Solvent: C1CCOC1
Product: CCCCCCOc1ccc(C2CC=C(c3ccc(C4CC=C(c5ccc(OCCCC)c(F)c5F)CC4)c(F)c3F)CC2)c(F)c1F
Temperature: 30 °C
Reaction time: 2 h

Procedure:
1-Butoxy-4-(4-(2,3-difluorophenyl)cyclohex-1-enyl)-2,3-difluorobenzene (s-20) (8.1 g) and THF (200 ml) were put in a reaction vessel under an atmosphere of nitrogen and cooled to −74° C. sec-Butyllithium (a 1.00 M solution in n-hexane and cyclohexane; 26.0 ml) was added dropwise thereto in the temperature range of −74° C. to −70° C., and the stirring was continued for another 2 hours. Then, 4-(2,3-difluoro-4-hexyloxyphenyl)cyclohexanone (s-14) (20.0 g) dissolved in THF (100 ml) was added dropwise thereto in the temperature range of −75° C. to −70° C., and the stirring was continued for another 8 hours while the mixture was allowed to come to 25° C. The reaction mixture was poured into a vessel containing an aqueous solution of ammonium chloride (3%; 100 ml) and ethyl acetate (100 ml), and mixed with them. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and the extraction was carried out. The combined organic phase was washed successively with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. p-Toluenesulfonic acid (0.14 g) and toluene (200 ml) was mixed with the residue and the mixture was heated to reflux for 2 hours, while distilled water was removed. After the reaction mixture had been cooled to 30° C., water (100 ml) and toluene (100 ml) were added to the mixture, and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction was carried out. The combined organic phase was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. The solution was purified by column chromatography using silica gel as a stationary phase powder and a mixed solvent of toluene/heptane (1/1 by volume) as an eluent, and then by recrystallization from a mixed solvent of ethyl acetate/Solmix A-11 (1/1 by volume) to give 1-butoxy-4-(4-(4-(4-(2,3-difluoro-4-hexyloxyphenyl)cyclohex-1-enyl)-2,3-difluo rophenyl)cyclohex-1-enyl)-2,3-difluorobenzene (No. 48) (0.61 g). The yield based on the compound (s-20) was 4.2%.