Acrylic Acid → 1,3-Bis(4-benzoyl-3-hydroxyphenoxy)-2-propyl acrylate

Participants

Reaction Steps

3 g of trifluoromethanesulfonic acid, 0.1 g of hydroquinone and 0.1 g of hydroquinone monomethyl ether were added to a solution of 48.5 g (0.1 mole) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-2-propanol and 43.6 g (0.6 mole) of acrylic acid in 600 ml of toluene, and the solution was heated for 3 hours at a temperature of 105° to 110° C. After cooling to room temperature, the reaction mixture was washed with 1.5 liters of water. The toluene was then distilled off from the reaction mixture under a pressure of 20 mbar. The oily residue remaining was dissolved in hot ethanol. Cooling this solution to room temperature gave 40 g (75 percent of theory) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl acrylate in the form of colorless crystals having a melting point of 98° to 100° C. and a purity of 99 percent (HPLC). The UV spectrum gave two absorption maxima at wave lengths of 287 nm (extinction 0.520; extinction coefficient 28,100) and 324 nm (extinction 0.335; extinction coefficient 18,100).

Provenance & Evidence