Hydrochloric Acid → HCID 178447839, compound

Participants

Reaction Conditions

Reaction Steps

First, 46 g of 1,2-difluorobenzene and 240 ml of dehydrated tetrahydrofuran were put in an argon-replaced 2 flask, and cooled to −60° C. Then 315 ml of a hexane solution containing n-butyllithium at a concentration of 1.6 mol/l was dropped into the resultant mixture while being stirred for one hour, and further stirred keeping the same temperature for two hours. Subsequently, 470 ml of dehydrated tetrahydrofuran containing 80 g of 4-(trans-4-propylcyclohexyl)cyclohexane dissolved therein was dropped and stirred keeping the same temperature for two hours. The resultant mixtures was left to gradually resume room temperature, stirred for eight hours and cooled again to 0° C. The reaction solution was poured into dilute hydrochloric acid to acidify the reaction solution. Toluene was added to the resultant solution for extraction. The resultant toluene layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue, 2 g of p-toluenesulfonic acid, and 1 of toluene were put in a 2 flask provided with a water content quantitative tube, and subjected to azeotropic dehydration under reflux for five hours. After the reaction, the reaction solution was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was distilled (b.p. 151° C./16 Pa) and recrystallized from acetone to obtain 55.7 g (Y: 48.6%) of 1,2-difluoro-3-[4-(trans-4-propylcyclohexyl)cyclohexenyl]benzene. The purity of the resultant compound was 98.0% as measured by GC.

Provenance & Evidence