反应详情

A solution of p-dibromobenzene (5.6 g, 0.024 mol) dissolved in tetrahydrofuran (200 ml) was dropwise added to sliced Mg (1.2 g, 0.049 mol) in nitrogen current so as to give soft reflux. After 7 hours, the reaction finished to yield its magnesium bromide, to which a solution of 4-(trans-4-propylcyclohexyl)-cyclohexanone (10.9 g, 0.049 mol) dissolved in tetrahydrofuran (100 ml) was rapidly dropwise added while the temperature was kept at 30° C. or lower. After the addition, the mixture was refluxed for 1.5 hour and 3N hydrochloric acid was added. The reaction liquid was extracted with toluene (100 ml×3), combined toluene layers were washed with water and the solvent was distilled off under reduced pressure. The remaining oily substance was 1,4-bis[4-(trans-4-propylcyclohexyl)-cyclohexan-1-ol]benzene, to which potassium hydrogen sulfate (2.5 g) was added, followed by dehydrating at 200° C. for 2 hours in nitrogen current, cooling, adding toluene (300 ml), filtering off potassium hydrogen sulfate, washing toluene layer with water, distilling off the solvent under reduced pressure and recrystallizing the residue from toluene to obtain an objective product, 1,4-bis[4-(trans-4-propylcyclohexyl)cyclohexen-1-yl]benzene (yield: 0.9 g) having a C-Sm point of 98.5° C. and a Sm-I point of 300° C. or higher.

1. additionwas rapidly dropwise added while the temperature
2. customwas kept at 30° C.
3. additionAfter the addition
4. temperaturethe mixture was refluxed for 1.5 hour
5. customThe reaction liquid
6. extractionwas extracted with toluene (100 ml×3)
7. washwere washed with water
8. distillationthe solvent was distilled off under reduced pressure
9. additionto which potassium hydrogen sulfate (2.5 g) was added
10. temperaturecooling
11. additionadding toluene (300 ml)
12. filtrationfiltering off potassium hydrogen sulfate
13. washwashing toluene layer with water
14. distillationdistilling off the solvent under reduced pressure
15. customrecrystallizing the residue from toluene