Water → HCID 178447923, compound

Participants

Reaction Steps

In a nitrogen atmosphere, 132 g of crude 1-(1-hydroxy-4-propylcyclohexyl)-3,5-difluorobenzene and 2.99 g of p-toluenesulfonic monohydrate were dissolved in 250 mL of toluene, and the resultant solution was stirred for 2 hours under reflux while the produced water was removed. After the solution was allowed to cool to room temperature, an organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. Then, the whole amount of the resultant residue was dissolved in 280 mL of ethyl acetate, and 7.1 g of palladium 5%/carbon was added to the solution, followed by stirring in a hydrogen atmosphere at 5 Mpa for 6 hours. After the palladium catalyst was filtered off, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. Then, the whole amount of the resultant product and 3.39 g of tertiary butoxypotassium were dissolved in 350 mL of DMF, followed by stirring at room temperature for 4 hours. Then, water and hexane were added to separate an organic layer. Further, an aqueous layer was subjected to extraction with hexane, and the hexane extract was combined with the organic layer and washed with saturated brine. The resultant mixture was dried by adding sodium sulfate, the solvent was distilled off, and distillation under reduced pressure (206 Pa, b. p.=110° C. to 112° C.) yielded 58.05 g of 1-(trans-4-propylcyclohexyl)-3,5-difluorobenzene.

Provenance & Evidence