[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][C:11](=[CH:14][O:15]C)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)=O.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH:14]=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1The compound (36) (45.0 g), formic acid (87%; 54.0 g), and toluene (250 ml) were mixed, and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled to 30° C., and then water (200 ml) and toluene (200 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and light yellow solids. The residue was dissolved in toluene (50 ml). The solution was added to a mixture of 5.0 g of 95% sodium hydroxide and 200 ml of Solmix A-11 cooled to 7° C., and the solution obtained was stirred at 10° C. for 2 hours. Then, an aqueous 2N-sodium hydroxide solution (100 ml) was added thereto, and the mixture was stirred at 5° C. for 2 hours. The reaction mixture obtained was poured into a mixture of water (200 ml) and toluene (200 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and an extractive operation was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue obtained was concentrated and purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder and dried, giving 39.8 g of 1-(3-fluorophenyl)-trans-4-cyclohexanecarboaldehyde (37). The yield based on the compound (36) was 94.5%.
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