1-Iodooctane → 2-(4-Decyloxyphenyl)-5-octyloxybenzoxazole

Participants

Reaction Steps

In a 20 ml-round-bottomed flask, 0.25 g (0.68 mM) of 2-(4-decyloxyphenyl)-5-hydroxybenzoxazole, 0.08 g (1.21 mM) of potassium hydroxide and 3 ml of butanol were placed and heated to provide a solution. To the solution, 0.18 ml (1.00 mM) of octyl iodide was added, followed by heat-refluxing for 5 hours and 40 minutes under stirring. After the reaction, the solvent in the reaction mixture was distilled off under reduced pressure. To the residue, ethyl acetate and water were added, followed by stirring at room temperature. The organic layer was successively washed with 2%-sodium thiosulfate aqueous solution and water, followed by drying with anhydrous sodium sulfate and reduced pressure distillation. The resultant residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (acetone-methanol) to obtain 0.17 g of 2-(4-decyloxyphenyl)-5-octyloxybenzoxazole (Yield: 52.1%). ##STR82##

Provenance & Evidence