Benzaldehyde → Methyl 3-Hydroxy-2-methylene-3-phenylpropionate

Participants

Reaction Steps

106 g (1 mol) of benzaldehyde (available from Nakarai Tesk K. K.), 11.2 g (0.1 mol) of 1,4-diazabicyclo[2,2,2]octane (available from Nacalai Tesque Inc.), and 90 ml (1 mol) of methyl acrylate (available from Nacalai Tesque Inc.) were stirred at room temperature over 7 days. To the reaction solution were then added 200 ml of a 6N hydrochloric acid and 200 ml of ethyl acetate so that an organic phase was extracted. The resulting organic phase was washed with a 10% brine, and then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was distilled under reduced pressure to obtain 167.8 g of the desired compound in the form of 99% purity colorless oily matter. When allowed to stand, the product was solidified. The product exhibited a melting point of from 34° to 36° C. (Yield: 87%)

Provenance & Evidence