Acetic Acid → Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoate

Participants

Reaction Steps

A solution of 151 g (1.00 mole) of 3-nitrobenzaldehyde, 116 g (1.00 mole) of methyl acetoacetate, 10 mL of glacial acetic acid, 4 mL of piperidine, and 400 mL of benzene was refluxed 2 hr during which time 21 mL of water was removed via a Dean-Stark trap. The dark yellow solution was cooled to ambient temperature and solidification occurred. Filtration followed by washing with ether afforded 180 g of product as a yellow solid. An additional 23 g product was obtained from the filtrate to yield a total of 203 g (82%) of product, m.p. 145°-146° C. (literature m.p., 158° C.; cf: Meyer, et al., Arzneim.- Forsch/Drug Research, 31, 407 (1981)).

Provenance & Evidence