Water → HCID 2748365, compound

Participants

Reaction Steps

To a solution of 140 g (0.71 mol) of deoxybenzoin and 170 g (1.7 mol) of ethyl acrylate in 2 L of absolute ethanol at ambient temperature was added in portions 20 mL of 50% aqueous sodium hydroxide. An additional 170 g (1.7 mol) of ethyl acrylate was then added over a 15 min. period. The mixture was stirred vigorously for 2.5 h, poured into 1 L of water and extracted with 3×1 L of ether. The organic layers were combined, washed with water and brine, and dried over sodium sulfate. The filtrate was concentrated to near dryness, triturated with 1.5 L of pentane, filtered and the filtrate allowed to stand at -20° C. giving 145 g (69%) of ethyl 4,5-diphenyl-5-oxopentanoate as a white solid (top 45°-57° C.).

Provenance & Evidence