Hydrochloric Acid → 4-Propyl-1-(3-fluorophenyl)-cyclohexanol

関与物質

反応手順

3-Fluorobromobenzene (8) (10.0 g) and THF (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to −74° C. n-Butyllithium (1.57 M, in a n-hexane solution; 40.0 ml) was added dropwise thereto in the temperature range of −74° C. to −70° C., and the mixture was stirred for another 2 hours. Subsequently, 4-propylhexanone (16) (12.0 g) in a THF (50 ml) solution was added dropwise thereto in the temperature range of −74° C. to −65° C., and the mixture was stirred for another 8 hours while allowing the temperature to come to 25° C. The reaction mixture obtained was poured into a vessel containing a 1N—HCl solution (500 ml) and ethyl acetate (300 ml), and mixed. 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 water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Subsequently, the solvent was distilled off under reduced pressure, giving 13.5 g of 4-propyl-1-(3-fluorophenyl)-cyclohexanol (18). The compound (18) obtained was a yellow oil.

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