Hydrochloric Acid → HCID 178443902, compound

Participants

Reaction Conditions

Reaction Steps

An ethyl ether solution (30 ml) of 2-(trans-4-n-hexylcyclohexyl)-5-cyanopyridine (13.2 g) of Example 16 was added to an ethyl ether solution (50 ml) of a Grignard reagent prepared from metallic Mg (2.5 g) and butyl bromide (13.8 g), followed by agitating the mixture at 35° C. for 5 hours, pouring the resulting solution in ice water containing 6N-HCl aqueous solution (100 ml), adding 2N-NaOH aqueous solution till the solution became basic, adding toluene (300 ml) to the resulting solution, washing the separated organic layer with water till the washing water became neutral, distilling off the solvent, and recrystallizing the residue from methanol to obtain 2-(trans-4-n-hexylcyclohexyl)-5-valeroylpyridine (4.3 g). This compound exhibited smectic phase between 46° C. and 66° C. To this compound were added m-chloroperbenzoic acid (4.6 g) and chloroform (50 ml), followed by agitating the mixture at room temperature for one week, filtering off the resulting precipitates, adding phosphorus oxychloride (10 ml) and toluene (50 ml) to the precipitates, heating the mixture at 80° C. for 2 hours, distilling off the solvent, adding warm water (100 ml), adding 2N-NaOH aqueous solution till the solution became basic, adding toluene (100 ml), washing the separated organic layer with water till the washing water became neutral, and distilling off the solvent to obtain 2-(trans-4-n-hexylcyclohexyl)-5-valeroyloxypyridine. To this compound were added KOH (1.5 g) and ethylene glycol (50 ml), followed by heating the mixture at 150° C. for 8 hours, cooling, adding water (100 ml), adding acetic acid till the solution became acidic, filtering off the resulting precipitates, and recrystallizing from methanol to obtain 2-(trans-4-n-hexylcyclohexyl)-5-hydroxypyridine. This compound was dissolved in ethanol (30 ml), followed by adding ethyl iodide (1.0 g), KOH (0.3 g) and water (2 ml), heating the mixture at 65° C. for 5 hours, cooling, adding water (100 ml) and toluene (50 ml), washing the separated organic layer with water till the washing water became neutral, and distilling off the solvent from the organic layer to obtain the objective 2-(trans-4-n-hexylcyclohexyl)-5-ethoxypyridine.

Provenance & Evidence