Diethyl Oxalate → Ethyl 3-oxo-3-[3-(trifluoromethyl)phenyl]propanoate

Participants

Reaction Steps

A mixture of 1.96 g (0.0275 mol) sodium ethoxide (95%) and 22 ml ethanol was stirred 20 minutes at room temperature and was then cooled with an ice bath. 3.65 g (0.025 mol) diethyloxalate followed by 4.7 g (0.025 mol) 1-(3-trifluoromethyl-phenyl)-ethanone were added slowly. The mixture was stirred for 30 min. at 0-5° C., then allowed to warm to room temperature and additional 25 ml ethanol were added. After 1 d at room temperature the solvent was evaporated. Water and diethylether were added to the residue. The organic phase was separated and the aqueous phase was extracted one more time with diethyl ether. The aqueous phase was acidified with 2M HCl to pH2 and extracted three times with diethyl ether. The combined organic phases were dried over magnesium sulfate, the solvent was evaporated and the residue triturated with petrol ether to give 5.35 g (0.0185 mol) 3-oxo-3-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester.

Provenance & Evidence