Hydrochloric Acid → HCID 55115836, compound

Participants

Reaction Conditions

Reaction Steps

In a nitrogen atmosphere, a solution prepared by dissolving 75.85 g of 3,5-difluorobromobenzene in 150 mL of THF was added at a rate that caused gentle reflux to a solution prepared by suspending 10.03 g of magnesium in 50 mL of THF, followed by stirring at 40° C. for 1 hour. After the resultant mixture was allowed to cool to room temperature, a solution prepared by dissolving 60.62 g of 4-propylcyclohexanone in 120 mL of THF was added to the mixture at such a rate that the inside temperature did not exceed 35° C., followed by stirring at room temperature for 2 hours. Then, 10% hydrochloric acid was added until the reaction system became acidic, and an organic layer was separated from the mixture. Further, an aqueous layer was subjected to extraction with toluene, and the toluene extract was combined with organic layer and washed with saturated brine. The resultant mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure to yield 132 g of crude 1-(1-hydroxy-4-propylcyclohexyl)-3,5-difluorobenzene.

Provenance & Evidence