Acetic Acid → 4-(Acetyloxy)-2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, ethyl ester

Participants

Reaction Steps

A solution of ethyl 4-acetoxyacetoacetate (23.0 g, 0.122 mole, Tet., 28, 967 (1972)) and 3-nitrobenzaldehyde (18.47 g, 0.122 mole) in 125 ml of benzene was treated with HOAc (0.6 ml) and piperidine (0.6 ml) and heated at reflux temperature. Collection of water ceased after 0.5 hour; therefore, additional HOAc (1 ml) and piperidine (1 ml) were added and refluxing continued. A total of 2.0 ml water was collected. The cooled mixture was washed with water (2x) and saturated brine, dried over anhydrous magnesium sulfate, treated with Darco to remove color and concentrated in vacuo to give an oil that solidified on standing. Trituration with IPE/Et2O/Hexane and stirring overnight to pulverize the solids afforded 24.2 g of the title

Provenance & Evidence