Hydrochloric Acid → 1,2,3-triphenylpropane-1,3-dione

Participants

Reaction Conditions

Reaction Steps

In a 500-ml four-necked flask were placed 16.0 g (0.40 mole) of 60% sodium hydride (an oil-added grade), 39.6 g (0.20 mole) of deoxybenzoin, 200.0 g of toluene, and 198.8 g (1.46 moles) of methyl benzoate. The mixture was then heated under reflux with stirring for 15 hours while distilling off methanol. After the reaction was over, the reaction mixture was cooled to 40° C. and 60.8 g (0.60 mole) of concentrated hydrochloric acid and 180.0 g of water were added in drops. The reaction mixture was transferred to a separatory funnel and an organic layer was separated. The organic layer was concentrated under reduced pressure to dryness. The residue was purified by reslurrying with methanol and a solid was recovered by filtration and dried under reduced pressure to give 36.2 g of 1,2,3-triphenylpropane-1,3-dione.

Provenance & Evidence