Diethyl methylmalonate → HCID 18938223, compound

Participants

Reaction Conditions

Reaction Steps

104 g (0.6 mol) of diethyl methylmalonate were added dropwise at room temperature to 13.8 g (0.6 mol) of sodium in 300 cm3 of H2 O-free EtOH. Subsequently, 178 g (0.6 mol) of 2-(3-quinolyl)benzyl bromide were added dropwise and the mixture was heated under reflux for 3 hours. At room temperature, 100 g (1.8 mol) of KOH dissolved in 400 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 145 g (83%) of 2-(2-(3-quinolyl)benzyl)propionic acid as solid.

Provenance & Evidence