Sodium Iodide → Ethyl 3-{4-[(prop-2-en-1-yl)oxy]phenyl}propanoate

Participants

Reaction Steps

38.8 g (0.2 mol) of ethyl phloretate (prepared from commercial phloretic acid (e.g. Merck, D-64271 Darmstadt, DE) by esterification with ethanol) were dissolved in 20 ml of acetone, and 36.3 g (0.3 mol) of allyl bromide, 48.3 g (0.35 mol) of potassium carbonate and 0.05 g of sodium iodide were added. The mixture was heated at reflux for 7 h and cooled, and the excess of carbonate was filtered off. Concentration of the filtrate gave ethyl 3-(4-allyloxyphenyl)propionate, which was hydrolyzed in customary manner with methanolic potassium hydroxide to give the free acid. Customary reaction of the acid with thionyl chloride in toluene at 80° C. gave the 3-(4-allyloxyphenyl)propionyl chloride (b.p. 0.01 hPa: 106-108° C.) in 93% yield. 51.2 g (0.22 mol) of this acid chloride and 39.2 g (0.22 mol) of hydroquinone monomethacrylate were dissolved in 300 ml of toluene at 65° C. 24.0 g (0.24 mol) of triethylamine were added dropwise with stirring, and the mixture was subsequently stirred for 3 h. After cooling, the amine hydrochloride was filtered off and the filtrate was worked up in a customary manner. Concentration of the organic residue and recrystallization of the solid residue from toluene/benzine (b.p. 100-140) gave 4-methacryloyloxyphenyl) 3-(4-allyloxyphenyl)propionate in 80% yield. The ester melts at 67° C.

Provenance & Evidence