反应详情

温度

60 °C

THF (20 ml) was added to sodium hydride (55%) (1.7 g) and the solution was cooled, followed by adding to the solution, a solution of 4'-hydroxy-4-octyloxy-biphenyl (8 g) in THF (100 ml), successively adding a solution of 2S-2-(2'-tetrahydropyranyloxy)-4-methyl-pentyl-p-toluenesulfonate (10 g) obtained above in the item 2 in N,N-dimethylformamide (hereinafter abbreviated to DMF) (200 ml), heating the mixture at 80°-90° C. for 8 hours, cooling the resulting material, adding toluene (300 ml), washing with water, then with an alkali and further with water, concentrating, purifying the concentrate according to column chromatography using a column having activated alumina filled therein and using toluene as an eluent, concentrating the resulting elute, adding ethanol (300 ml), further adding 12M+HCl (5 ml), heating the mixture at 60° C. for 2 hours, cooling, filtering off the resulting solids, and recrystallizing from a mixed solution of ethanol with ethyl acetate to obtain S -1-(4'-octyloxy-4-biphenylyloxy)-4-methylpentan-2-ol ([α]D24 +8.2 (C 0.54, CHCl3)) (8 g). This product exhibited phase transition points of C 95° C. (S5.58° C.), S4.103° C., S3.113.1° C., S2.113.6° C., S1.115.6° C., SA.119.5° C. and I wherein C represents crystalline phase; I , isotropic liquid phase; SA, smectic A phase; S1 -S5, smectic phases whose attributions are at present unknown; and (), monotropic phase.

1. temperaturethe solution was cooled
2. additionby adding to the solution
3. temperatureheating the mixture at 80°-90° C. for 8 hours
4. temperaturecooling the resulting material
5. washwashing with water
6. concentrationwith an alkali and further with water, concentrating
7. custompurifying the concentrate
8. additionfilled
9. concentrationconcentrating the resulting
10. washelute
11. additionadding ethanol (300 ml)
12. additionfurther adding 12M+HCl (5 ml)
13. temperaturecooling
14. filtrationfiltering off the resulting solids
15. customrecrystallizing from a mixed solution of ethanol with ethyl acetate