Ethanol → 3-(2-phenylphenyl)propionic acid

Participants

Reaction Conditions

Reaction Steps

93 cm3 (0.61 mmol) of diethyl malonate dissolved in 50 cm3 of H2P-free EtOH were added dropwise at room temperature to 14 g (0.61 mmol) of sodium in 400 cm3 of H2O-free EtOR. 150 g (0.61 mmol) of 2-phenylbenzyl bromide in 200 cm3 of H2O-free EtOH were subsequently added dropwise, and the mixture was refluxed for 3 hours. 102 g (1.83 mol) of KOH dissolved in 150 cm3 of H2O were added at room temperature, and the mixture was refluxed for a further 4 hours. The solvent was removed in vacuo, H2O was added to the residue until the latter dissolved completely, and the mixture was acidified to pH 1 by means of concentrated aqueous HCl. The precipitate which formed was filtered off with suction, dried and heated at 130° C. for 1 hour, giving 112 g (81%) of 8 as a viscous oil.

Provenance & Evidence