Toluene → 8-[2-Fluoro-4-(4'-pentyl-1,1'-bicyclohexane-4-yl)phenyl]-1,4-dioxaspiro[4,5]decan-7-ene

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Reaction Steps

The compound (T-5) (29.4g), p-toluenesulfonic acid monohydrate (1.47 g) and toluene (800 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 120 minutes while water being distilled was removed. After cooling to room temperature, the reaction mixture was washed sequentially with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure and the residue was purified by means of column chromatography (silica gel; toluene), giving 8-[2-fluoro-4-(4′-pentyl-1,1′-bicyclohexane-4-yl)phenyl]-1,4-dioxaspiro[4,5]decan-7-ene (T-6) (20.5 g). The yield based on the compound (T-4) was 72%.

Provenance & Evidence