Hydrochloric Acid → HCID 178458228, compound

Participants

Reaction Steps

In a mixture of 0.7 g (60% oiliness, corresponding to 18.2 mmol) of sodium hydride and 5 ml of dimethyl formamide (DMF) was added by drops a solution of 4.0 g (15.1 mmol) of the 3,3′-difluoro-4′-hydroxy-4-propoxybiphenyl obtained in the previous step in 20 ml of DMF at room temperature, and then stirred at the same temperature for 1 hour. Subsequently, a solution of 6.0 g (22.7 mmol) of trans-4-propyl-l-iodomethylcyclohexane in 20 ml of DMF was added by drops to the reaction solution at room temperature, stirred at the same temperature for 1 hour, and then heated to reflux for 3 hours. After finishing of the reaction, the reaction solution was poured into 50 ml of a diluted hydrochloric acid and then extracted with 150 ml of toluene. The organic layer thus obtained was washed with a diluted aqueous sodium hydroxide solution thrice and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (eluent: heptane/toluene=7/3) to obtain 2.3 g of a crude 3,3′-difluoro-4′-((trans-4-propylcyclohexyl)methoxy)-4-propoxybiphenyl. This product was recrystallized from mixed solvent of ethanol/ethyl acetate (7/3) to obtain 1.8 g of the subject compound. (Yield: 48.2%)

Provenance & Evidence