Water → Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate

Participants

Reaction Steps

19.8 g (0.0795 mol) of ethyl α-(p-methoxyphenyl)-β-(dimethylamino)acrylate were dissolved in 740 ml of ethanol, in a 1 liter glass reactor, 30.6 9 of Pt/C type 18 catalyst (4.83% Pt and 59.70% water) were added, the mixture was first purged with nitrogen and then with hydrogen and finally a pressure of 600 psi H2 was applied. The mixture was left hydrogenating for 23 hours, was then filtered through Celite® 535 and was washed with 2×165 ml of ethanol. The ethanol was then removed under vacuum. The residue was dissolved in 30 ml of dichloromethane and was extracted with 50 ml and 2×15 ml of 2N hydrochloric acid. The operation continued with the acid aqueous phase that was basified with 40 ml of aqueous sodium hydroxide solution to pH 11. The product was extracted with 4×35 ml of ethyl acetate. The pooled organic phases were dried with sodium sulfate, filtered and evaporated to dryness under vacuum to give a pale yellow oil weighing 14.7 g, corresponding to ethyl α-(p-methoxyphenyl)-β-(dimethylamino)propionate (Yield: 74%).

Provenance & Evidence