Potassium Hydroxide → (+/-)-2-(2(1-Naphthyl)benzyl)propionic acid

Participants

Reaction Conditions

Reaction Steps

75 g (0.43 mmol) of dimethyl methylmalonate dissolved in 50 cm3 of H2O-free EtOH are added dropwise at room temperature to 10 g (0.43 mmol) of sodium in 100 cm3 of H2O-free EtOH. Subsequently, 140 g (0.43 mmol) of 7 in 200 cm3 of H2O-free EtOH were added dropwise and the mixture was heated under reflux for 3 hours. 85 g (1.3 mol) of KOH dissolved in 100 cm3 of H2O were added at room temperature and the mixture was heated under reflux for a further 4 hours. The solvents were removed under reduced pressure, the residue was admixed with H2O until completely dissolved and acidified with concentrated aqueous HCl to a pH of 1. The precipitate formed was filtered off with suction, dried and heated at 130° C. for 1 hour. This gave 96 g (77%) of 8 as a viscous oil.

Provenance & Evidence