Methanol → monoMethyl succinate

참여 물질

반응 조건

반응 단계

To a single-necked, 100 mL round-bottom flask equipped with a teflon stirbar, is added 20 g succinic anhydride dissolved in 50 mL methanol. The flask is equipped with a reflux condenser topped with a septa and argon balloon, and the reaction mixture is heated to reflux (70° C.) in an oil bath (Dow Corning Fluid) for a 16 hr time period. The reaction flask is then allowed to cool to room temperature, the stirbar removed, and the excess methanol removed via rotary evaporator to give 26.4 g of succinic acid monomethyl ester. In the same 100 mL flask containing succinic acid monomethyl ester is added a teflon stirbar, 35 mg palladium dichloride, 1.31 g triphenylphosphine, and 38 mL acetic anhydride, respectively. The flask is equipped with a short-path distillation apparatus with a thermometer, argon balloon, and an attached 100 mL collecting flask in an ice-bath. The reaction flask is heated to a temperature of 230° C. in an oil bath over a 30-40 minute time period, distilling out the excess acetic anhydride, acetic acid byproduct, and methyl acrylate. The reaction is complete after approximately 30 min heating at 230° C. when no more product distills and the solution darkens to a black color due to inactivation of the catalyst. The distillate is then analyzed by NMR to verify the presence of methyl acrylate. The reaction flask is cooled and weighed to determine how much starting material was removed due to reaction (17.9 g, 68% conversion to methyl acrylate).

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