Sulfuric Acid → Benzoic acid, 4-[3-(4-aminophenyl)propyl]-, methyl ester

Participants

Reaction Steps

To a mixture of 5.0 g of methyl 4-[3-(4-nitrophenyl)-3-oxoprop-1-en-1-yl]benzoate and 150 mL of methanol was added dropwise 5.0 mL of concentrated sulfuric acid under ice cooling. In an argon atmosphere, 500 mg of 10% palladium carbon was added to the reaction mixture. After hydrogen (3 atm) purging was performed at room temperature, the mixture was stirred for 24 hours. The insoluble material was removed by filtration by using celite, and then the filtrate was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue under ice cooling to neutralize the residue, and then extraction was performed using ethyl acetate. The organic layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform), thereby obtaining 2.9 g of methyl 4-[3-(4-aminophenyl)propyl]benzoate.

Provenance & Evidence