Potassium Carbonate → Methyl 2-benzylidene-3-hydroxypropionate

Participants

Reaction Steps

A crude product (5.99 g, 25.57 mmols) of methyl 2-benzylidene-3-acetoxypropionate was dissolved in 26 ml of methanol, and 3.53 g (25.5 mmols) of potassium carbonate were added thereto. The mixture was stirred at room temperature for 1 hour. Insoluble matters were separated by filtration, and the resulting solution was concentrated under reduced pressure. To the resulting residue were added 30 ml of water and 40 ml of toluene to extract an organic layer. The thus-obtained organic layer was washed with 30 ml of water and with 30 ml of a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (silica gel 100 g, mixture of hexane and ethyl acetate at a ratio of from 3:1 to 2:1) to obtain 3.02 g (15.71 mmols) of the above title compound (yield: 61.4%).

Provenance & Evidence