Toluene → 1-(4'-Octyloxy-4-biphenylyloxy)-4-methylpentan-2-ol

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence