beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene → 1-(2-Trifluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane
Reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[C:20]([F:27])[C:19]=3[C:28]([F:31])([F:30])[F:29])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]>[C].[Pd]>[F:31][C:28]([F:29])([F:30])[C:19]1[C:20]([F:27])=[C:21]([O:24][CH2:25][CH3:26])[CH:22]=[CH:23][C:18]=1[CH2:17][CH2:16][CH:13]1[CH2:14][CH2:15][CH:10]([CH:7]2[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]2)[CH2:11][CH2:12]1Participants
3
Procedure
7.89 g of β-(4-(4-propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene obtained in Example 7 was dissolved in 200 ml of a mixed toluene-solmix solvent. A palladium carbon catalyst was added to the solution in a nitrogen atmosphere and a hydrogenation reaction was conducted at ambient temperature and pressure for 2 hours. After the completion of the reaction, the catalyst was removed by filtration. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (eluent: heptane:toluene=4:1) to obtained 1-(2-trifluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane. This was further recrystallized twice from a heptane/ethanol mixed solvent to obtain 5.35 g of pure 1-(2-trifluoromethyl-3-fluoro-4-ethoxyphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane. The compound showed a liquid crystal phase and the transition point was as described below.