Uses
4-(6-Acryloyloxyhexyloxy)-benzoesure (4-cyanophenylester) can be used as an intermediate in organic synthesis, mainly used in laboratory research and development and in the process of chemical and pharmaceutical synthesis.
Synthesis
The target monomer was prepared by firstly converting the
acid into the corresponding acid chloride, then condensing this
withp-cyanophenol. The acid (17.32 g, 0.059 mol) was stirred with thionyl chloride (35.7 g, 0.3 mol) in the presence of DMF
(2 drops) and 2,6-di-tert-butyl-4-methyl phenol (4.4 g, 0.02
mol). After ca. 25 min, by which time solution was achieved,
the excess thionyl chloride was removed by rotary evaporation
and high vacuum (1-2 h). The acid chloride residue was dis-
solved in anhydrous chloroform (30 mL), then added slowly
dropwise into a stirred solution of p-cyanophenol (7.03 g,
0.059 mol) and triethylamine (6.07 g, 0.06 mol) in chloroform
(20 mL) at 0??C. After the addition the mixture was stirred at
room temperature for 24 h and then chloroform (200 mL)
added. This solution was washed with water (50 mL) followed
by 2 N sodium hydroxide solution (3 x 50 mL) and water (2 x
50 mL). The organic layer was dried (MgSO,), evaporated,
then subjected to flash chromatography, using dichloro-
methane as both the solvent and the eluant. The monomer was
finally recrystallized from isopropanol and shown to be pure
by tlc. Yield: 16 g, 69%.
