3′,4′-Dimethoxycinnamic acid

3,4-Dimethoxycinnamic acid (O-Methylferulic acid) is a monomer extracted and purified from Securidaca inappendiculata Hassk. 3,4-Dimethoxycinnamic acid exerts anti-apoptotic effects on L-02 cells via the ROS-mediated signaling pathway[1]. Anti-apoptotic effects[1].

General procedure: To aromatic aldehyde (500 mg, 1.0 equiv) and malonic acid (981 mg, 2.0 equiv) was added DABCO (105 mg, 2 equiv) in dimethyl formamide (5 mL) and the reaction mixture was stirred at 100-110 °C for 60-90 min. After completion of the reaction (TLC monitoring), reaction mixture was poured in water and then extracted with ethyl acetate. Crude product was recrystallized from chloroform/hexane system to provide cinnamic acids in good yield.To a solution of 1000 g (6.024 mol) of 3, 4-dimethoxybenzaldehyde in 3L pyridine, 1378.3 g (13.25 mol) of malonic acid and 100 mL of piperidine were added. The resulting mixture was stirred at 105 °C to 1 10 °C for 6 - 8 h. After completion of the reaction, the reaction mixture was cooled to 25 °C to 30 °C and slowly quenched the reaction mixture into 10 L of 5 percent sodium hydroxide solution at 25 °C to 30 °C (pH: 9- 10). The reaction mixture was washed with ethyl acetate (2 x 5 L) and the organic layer separated was washed with 2 L of 5 percent sodium hydroxide solution. The aqueous layers were combined and cooled to 15 °C to 20 °C. The aqueous layer was acidified slowly with 2.5 L of 50 percent sulphuric acid below 20 °C (pH: 1-2). After an additional 30 - 45 min stirring at 15 °C to 20 °C, the solid obtained was collected by filtration, washed with 10 L of water followed by 4 L of n-hexane. The partially dried compound was unloaded into trays and dried at 55 °C to 60 °C for 8-10 h to give 1 1 10 g of the title compound.Yield: 1 1 10 g (88 percent); 100 g of a three-necked reaction flask was charged with 25 g (240 mmol)Malonic acid, 33.2 g (200 mmol)3, 4-dimethoxybenzaldehyde, 40 ml (496 mmol) of pyridine, 2 ml (20.4 mmol) of hexahydropyridine, Heated to 75 ° C and then reflux 5h, Reaction is completed, Cooling 10min, 150 ml of 3 mol / ml of ice hydrochloric acid solution was added, Place the night, Filter, The precipitate was washed with 1000 ml of water, Get white crude.The crude product was recrystallized from absolute ethanol, A mixture of 37.0 g of pure white 3, 4-dimethoxyphenylacrylic acid, Yield 88.9percent.1. In a 100 ml three-necked flask, 6.24 g (60 mmol) of malonic acid, 8.3g (50 mmol) of 3, 4-dimethoxybenzaldehyde, 10 ml (124 mmol) of pyridine and 0.5 ml (5.1 mmol) of piperidine were heated 85°C for 4h. After completion of the reaction, the solution was cooled for 10 min, 60 ml of 3 mol / ml ice hydrochloric acid solution was added, and the mixture was left to stand overnight. The precipitate was washed with 400 ml of water to give a white crude product. The crude product was recrystallized from absolute ethanol to give 9 g of white pure 3, 4-dimethoxyphenylacrylic acid in a yield of 86.5percent.Example 7

Used in pharmaceutical intermediates and organic synthesis intermediates