Sulfuric Acid → 4-octyloxy-4'-((S)-3-methyl-pentanoyl)biphenyl

Participants

Reaction Steps

Sliced Mg (12.4 g, 0.510 mol) and dry ether (50 ml) were placed in a three-neck flask in a dry nitrogen atmosphere and agitated, and to the mixture was dropwise added a solution obtained by dissolving (+)-2-methylbutyl bromide (prepared from (-)-2-methyl-1-butanol and phosphorus bromide) in dry ether (1 l), so as to keep the temperature of the system at 25° C. or lower. After completion of the dropwise addition, the mixture was allowed to stand at room temperature for 30 minutes, followed by dropwise adding a solution obtained by dissolving a commercially available product, 4-octyloxy-4'-cyanobiphenyl (IV) (129 g, 0.42 mol) in dry ether (1 l) so as to keep the temperature of the system at 10° C. or lower, thereafter refluxing for 4 hours, cooling pouring the reaction liquid in water (600 ml), further adding diluted sulfuric acid (conc. sulfuric acid 40 ml +water 80 ml, adding toluene (500 ml), transferring the mixture into a separating funnel, water-washing till the washing liquid became neutral, distilling off the solvent, distilling the residue under reduced pressure, collecting a fraction of bp 245°~255° C./4 mmHg and recrystalling from acetone (30 ml) to obtain 4-octyloxy-4'-((S)-3-methyl-pentanoyl)biphenyl (IIIa1) (24.6 g), which was a smectic liquid crystal exhibiting SC* phase and SA phase, and its phase transition points were as follows as shown in Table 2, column of Example 23:

Provenance & Evidence