Synthesis of hydrosilylation epoxidized eugenol (HSI-EP-EU)

HSI-EP-EU was prepared from EP-EU as following procedure. The reaction of EP-EU (22.02 g, 0.1 mol) with triethylsilane (17.42 g, 0.15 mol) was conducted at a mol ratio of 1 : 1.5 (EP-EU versus triethylsilane) to a 50 mL round-bottom flask (karstedt catalyst solution catalyst: 10 ppm) equipped with a magnetic stirrer and a condenser. Then, the temperature was maintained at 100 °C, and triethylsilane was dropped into the mixture in 2 h. The reaction was taken for another 5 h to end the reaction and cooled down to the room temperature. Both xylene from the karstedt catalyst solution and the excess triethylsilane was then removed by distillation under reduced pressure. The resulting oil was purified by flash column chromatography (ethyl acetate/hexane, gradient 0–100% hexane) and dried under vacuum overnight to afford the title product as a clear, red-brown liquid (yield 87%). Epoxy value was 0.28. ¹H NMR (400 MHz, CDCl₃): δ = 6.88 (benzene ring, 1H), 6.83 (benzene ring, 1H) 6.70 (benzene ring, 1H), 4.19 (–CH₂–, 1H), 4.01 (–CH₂–, 1H) 3.85 (–CH₃, 3H), 3.37 (–CH–, 1H), 2.88 (–CH₂–, 1H), 2.71 (–CH₂–, 1H), 2.55 (–CH₂–, 1H), 1.85 (–CH₂–, 2H), 0.90 (–CH₃, 9H), 0.50 (–CH₂–, 8H) ppm.