Quinone → 2-Propenoic acid, 2-methyl-, 3-(chlorodimethylsilyl)propyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 40 milligrams of hexachloroplatinic acid and 1.0 gram of benzoquinone in 25 grams of allyl methacrylate was heated under anhydrous conditions in an oil bath to 60° C. Chlorodimethylsilane (24 milliliters) was then added slowly by a syringe. The hydrosilylation reaction was exothermic and the chlorodimethylsilane was added at a rate to maintain the temperature of the reaction between 58° C. and 62° C. Distillation of the reaction mixture afforded 4.8 grams of allyl methacrylate and 28.6 grams (81 percent yield based on recoverd starting material) of 3-(chlorodimethylsilyl)propyl methacrylate (bp 82° to 83° C. 0.5τ). This product was characterized by 1H NMR (CDCl3) δ0.34, s, 6H, SiCH3 ; 0.61 to 0.89, m, 2H CH2Si; 1.58 to 1.91, m, 5H, CH2CH3 ; 3.89 to 4.13, t, 2H, CH2 ; 5.52 to 5.35, t, 1H, vinylic; 5.89 to 6.07, t, 1H, vinylic.

Provenance & Evidence