4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

Chemical properties

White powder

Synthesis

14.0 g (58.8 mmol) of 4-(6-hydroxyhexyloxy)benzoic acid, 36.0 g (500 mmol) of acrylic acid, 2.00 g (11.7 mmol) of p-toluenesulfonic acid as an acid catalyst, and 1.20 g (11.8 mmol) of the polymerization inhibitor hydroquinone was dissolved in benzene. The mixed solution was refluxed in a flask connected to a Dean-Stark trap for about 12 hours until the amount of stoichiometry of water produced through the reaction was removed. After completion of the reaction, the solvent was distilled under reduced pressure, and the residue was dissolved in 300 mL of ethyl acetate. The mixed solution was washed with distilled water until no acrylic acid was found. At this time, the pH of the distilled water was checked to determine the presence of acrylic acid. Magnesium sulfate was added to the organic solution layer to dry the water. After filtration, the solvent was distilled under reduced pressure and recrystallized from isopropyl alcohol to obtain 4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid as a white powdery solid.