Toluene → 5-Hexylpyrimidin-2-yl 4-(hexyloxy)benzoate

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Reaction Steps

This 5-hexylpyrimidin-2-ol (1.8 g, 10 mmol) was dissolved in pyridine (2 ml), followed by adding dropwise to the solution, a toluene solution (30 ml) of p-hexyloxybenzoyl chloride (2.4 g, 10 mmol), stirring at 50° C. for 4 hours, further adding toluene (50 ml) to the reaction mixture to carry out extraction, washing the toluene layer twice with 6N-HCl aqueous solution (30 ml), further washing 5 times with 2N-NaOH aqueous solution (40 ml), washing with pure water until the aqueous layer became pH 7, drying the toluene layer over anhydrous Na2SO4 and distilling off toluene to obtain raw crystals (3.1 g) (yield 81%), which were then purified by activated alumina chromatography (solvent: toluene) and recrystallized from ethanol to obtain 5-hexylpyrimidin-2-yl p-hexyloxybenzoate (2.2 g) (yield 58%). This compound exhibited liquid crystallinity and as to their phase transition points, C-N point was 28.4° C. and N-I point was 35° C.

Provenance & Evidence