Phenothiazine → 2-Propenoic acid, 2-methyl-, 3-butenyl ester

Participants

Reaction Steps

To a 250 ml round-bottom flask, containing 3-buten-1-ol (24.7 g) and phenothiazine (0.1 g inhibitor), methyl methacrylate (80 ml) was added, followed by a methanolic solution of magnesium methoxide [prepared by dissolving magnesium metal (0.1 g) in anhydrous methanol (5 ml)]. The stirred mixture was slowly heated and methanol was distilled off (bp 64-70° C.) until the temperature at the distillation head rose to approximately 100° C. and the methyl methacrylate started to distill. The mixture was then cooled to room temperature and the solids were filtered off. The filtrate was fractionated under vacuum. Pure 3-butenyl methacrylate was collected at bp 63-66° C./30 mmHg. Yield: 22.5 g.

Provenance & Evidence