Ethanol → 3-Octylpyridine

Participants

Reaction Steps

To this 2-(m-fluoro-p-hydroxyphenyl)-5-octylpyridine (2 g, 0.007 mol) were added ethanol (20 ml), KOH (0.4 g, 0.007 mol) and optically active 5-methylheptyl bromide (1.4 g, 0.007 mol), followed by heating the mixture under reflux with stirring for 4 hours, cooling, adding water and toluene, transferring the mixture into a separating funnel, washing the resulting organic layer with 2N-NaOH aqueous solution, washing with water, distilling off the solvent under reduced pressure and recrystallizing the residue in a freezer to obtain the objective optically active (S)-2-p-5-methyl-heptyloxy-m-fluorophenyl)-5-octylpyridine (1.8 g). This product had the following phase transition C-Sc *: 33.0° C., Sc *-SA : 33.5° C., SA -I: 39.4° C. Further, the elemental analysis values accorded well with its calculated values as follows:

Provenance & Evidence