Diethyl methylmalonate → HCID 18938318, compound

Participants

Reaction Conditions

Reaction Steps

148 g (0.85 mol) of diethyl methylmalonate were added dropwise at room temperature to 19.5 g (0.85 mol) of sodium in 400 cm3 of H2 O-free EtOH. Subsequently, 211 g (0.85 mol) of 2-(2-pyridyl)benzyl bromide were added dropwise and the mixture was heated under reflux for 3 hours. At room temperature, 143 g (2.55 mol) of KOH dissolved in 500 cm3 of H2O were added and the mixture was heated under reflux for a further 4 hours. The EtOH was distilled off and the residue was admixed with H2O until completely dissolved and subsequently acidified with concentrated aqueous HCl to a pH of 1. The precipitate formed was filtered off with suction, dried and heated for 1 hour at 130° C. This gave 193 g (94%) of 2-(2-(2-pryridyl)benzyl)propionic acid as solid.

Provenance & Evidence