Benzene → Ethyl 2-Methyl-3-(2-Nitrophenyl)propenoate

Participants

Reaction Steps

Into 500 ml of benzene, 21.0 g (139.0 mmol) of 2-nitrobenzaldehyde (manufactured by Aldrich Chemical Co., Inc.) and 50.0 g (138.0 mmol) of Wittig reagent (carbethoxyethylidene triphenylphosphorane, manufactured by Aldrich Chemical Co., Inc.) were dissolved; and the mixture was stirred at room temperature for one night. After the completion of the reaction was verified by TLC, the reaction liquid was concentrated under a reduced pressure, and ethanol was added to the resulting residue. The crystal precipitated in this solution was filtered out, and the filtrate was concentrated under a reduced pressure, so as to yield an oily product, which was then refined by a silica gel column chromatography (silica gel; developing solvent: ethyl acetate/hexane=1/4), whereby 32.1 g of the aimed compound were obtained as an oily product (yield: 98.2%).

Provenance & Evidence