Diethylene Glycol → 4-octyloxy-4'-((S)-3-methyl-pentyl)biphenyl

4-Octyloxy-4'-((S)-3-methyl-pentanoyl)biphenyl (24.6 g, 0.065 mol) obtained in Example 23 described later, 80% hydrazine hydrate (50 ml) and diethylene glycol (85 ml) were placed in a 500 ml three-neck flask, followed by heating with stirring, keeping the mixture at 120° C. for one hour, then cooling, adding, at a stroke, a solution of potassium hydroxide (8.8 g, 0.157 mol) in water (5 ml) while keeping the temperature at 50° C., distilling off so that the temperature of the system might become 200° C., reacting at 200° C. for 4 hours, then cooling, adding water (200 ml) and toluene (50 ml), transferring the contents into a separating funnel, water-washing the organic layer till the washing liquid became neutral, distilling off the solvent, distilling under reduced pressure to collect a fraction having a boiling point of 210°~213° C./3 mmHg, and recrystallizing it from ethyl alcohol (20 ml) and ethyl acetate (5 ml) to obtain 4-octyloxy-4'-((S)-3-methyl-pentyl)biphenyl (IIIb1) (13.5 g) which was a smectic liquid crystal exhibiting SC* phase and SH* phase, and whose phase transition points were as follows as shown in Table 2, column of Example 24:

1. temperatureby heating
2. customat 120° C.
3. customfor one hour
4. temperaturecooling
5. additionadding, at a stroke
6. customat 50° C.
7. distillationdistilling off so that the temperature of the system
8. custommight become 200° C.
9. temperaturecooling
10. additionadding water (200 ml) and toluene (50 ml)
11. washwater-washing the organic layer till the washing liquid
12. distillationdistilling off the solvent
13. distillationdistilling under reduced pressure
14. customto collect a fraction
15. customrecrystallizing it from ethyl alcohol (20 ml) and ethyl acetate (5 ml)

ORD record

ord-1a164770ec224eafbc80dfc3dde7daea

Source dataset

uspto-grants-1986_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04614609