2-Propenoic acid, 3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl ester synthesis

Yield:-

Reaction Conditions:

with triethylamine;2,6-di-tert-butyl-4-methyl-phenol in tetrahydrofuran at 20;

Steps:

3 Synthesis of polymerizable liquid crystal compound (E1)

12.0 g of the intermediate compound (A2) obtained above was dissolved in 40 ml of THF along with 7.7 ml of triethylamine and a small amount of BHT and stirred at room temperature, in which a solution of 4.6 ml of acryloyl chloride in 40 ml of THF was dropped over 15 minutes under cooling on a water bath. After the dropping, the reaction solution was stirred for 30 minutes, after which the water bath was removed and stirring was continued overnight while returning to room temperature, followed by filtration of a precipitated TEA hydrochloride salt. About 3/4 of the THF was distilled off from the resulting filtrate, to which 50 ml of methylene chloride was added. The resulting organic phase was washed successively with 50 ml of a saturated sodium hydrogen carbonate aqueous solution, 50 ml of 0.5N-HCl and 50 ml of a saturated saline solution, and dried over magnesium sulfate, followed by distilling off the solvent to obtain a product. After recrystallization with ethanol, 6.0 g of compound (E1) was obtained. ¹H-NMR(CDCl₃) δ: 2.20(m, 2H), 4.10(t, 2H), 4.40(t, 2H), 5.81(d, 1H), 6.15(m, 1H), 6.41(d, 1H), 6.99(d, 2H), 7.55(d, 2H), 7.66(m, 4H).

References:

EP2062882,2009,A1 Location in patent:Page/Page column 22