Water → Methyl 3-(4-methylphenyl)-2-propenoate

Participants

Reaction Steps

To a solution of 3-(4-methylphenyl)-2-propenoic acid (10.0 g, 61.7 mmol) in THF (100 ml) were added 1,4-diazabicyclo[5.4.0]-7-undecene (11.0 mL, 73.6 mmol) and methyl iodide (4.3 mL, 69.1 mmol) under ice cooling and the mixture was stirred at room temperature for 24 hours. The resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with aqueous sodium sulfite, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane to obtain 9.10 g (yield 84%) of the title compound. mp. 56–58° C.

Provenance & Evidence