Acetic Acid → 4-{2-(4-Hexylphenyl)thiazole-5-yl}phenol

Participants

Reaction Steps

In a 300 ml-three-necked flask, 13.9 g (39.3 mM) of 2-(4-hexylphenyl)-5-(4-methoxyphenyl)1,3-thiazole, 76.5 ml of acetic acid and 69.5 ml of 47%-hydrobromic acid were placed, followed by heat-stirring for 16 hours at 100°-110° C. After the reaction, the reaction mixture was poured into cool water, followed by extraction with ethyl acetate. The organic layer was successively washed with water, 5%-sodium hydrogencarbonate aqueous solution and water, followed by drying and distilling-off of the solvent under reduced pressure. The residue was dissolved in a mixture solvent of ethanol/chloroform =1/1, followed by decolorization with activated carbon and distilling-off of the solvent under reduced pressure. The resultant residue was recrystallized two times from toluene to obtain 10.0 g of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)-1,3-thiazole (Yield: 75.8%).

Provenance & Evidence