1,4-Benzenedicarboxylic acid, 2-nitro-, 1,4-dimethyl ester

white powder

In a 1000 ml four-necked flask, 926.97 g of 98percent sulfuric acid was introduced, Stirring down to 10~15°C , Slowly add 97.7percent nitric acid 200.72g; Plus complete, keep 10~15 °C by adding dimethyl terephthalate 300.0g, about 30min plus, The reaction temperature was controlled at 15~20°C , After incubation for 30 minutes, The end point of the reaction was confirmed by TLC.After stirring for 15 minutes, the filter cake was rinsed with 900 ml of 5percent aqueous solution of sodium hydroxide and then rinsed with 500 ml of water to neutral. The filter cake was put into 3000 ml of water, and the mixture was stirred at room temperature for 30 minutes. Four bottles, add 1500g of ethanol for recrystallization: first heated to 50 ~ 55 , so that all the dissolved solids, and then cooled to 5 ° C below the full precipitation of the material; filtration, filter drying, the influx of goods 382.5g, 60°C dried in vacuo to obtain 351.2 g of white crystals in 95percent yield (as dimethyl dimethyl terephthalate), a gas chromatographic content of> 99percent, a melting point of 73.8 to 75.5 ° C (reported melting point: 73 to 76 ° C) .nitration reaction: electromagnetic stirring dimethyl terephthalic acid (compound I) 10g is dissolved in 50 ml concentrated sulfuric acid, ice-bath cooling, will 5 ml fuming nitric acid slowly dropping to the reaction flask, does not exceed the temperature is maintained during 20 °C; of after-reaction of adding 1h, TLC (thin layer chromatography) monitoring the consumption of raw materials, the reaction liquid stirring slowly poured into 100 ml ice water, separating white solid, filtering, the filter cake is washed with saturated NaHCOIn a 1000 ml four-necked flask, 926.97 g of 98percent sulfuric acid was introduced, Stirring down to 10~15°C , Slowly add 97.7percent nitric acid 200.72g; Plus complete, keep 10~15 °C by adding dimethyl terephthalate 300.0g, about 30min plus, The reaction temperature was controlled at 15~20°C , After incubation for 30 minutes, The end point of the reaction was confirmed by TLC.After stirring for 15 minutes, the filter cake was rinsed with 900 ml of 5percent aqueous solution of sodium hydroxide and then rinsed with 500 ml of water to neutral. The filter cake was put into 3000 ml of water, and the mixture was stirred at room temperature for 30 minutes. Four bottles, add 1500g of ethanol for recrystallization: first heated to 50 ~ 55 , so that all the dissolved solids, and then cooled to 5 ° C below the full precipitation of the material; filtration, filter drying, the influx of goods 382.5g, 60°C dried in vacuo to obtain 351.2 g of white crystals in 95percent yield (as dimethyl dimethyl terephthalate), a gas chromatographic content of> 99percent, a melting point of 73.8 to 75.5 ° C (reported melting point: 73 to 76 ° C) .nitration reaction: electromagnetic stirring dimethyl terephthalic acid (compound I) 10g is dissolved in 50 ml concentrated sulfuric acid, ice-bath cooling, will 5 ml fuming nitric acid slowly dropping to the reaction flask, does not exceed the temperature is maintained during 20 °C; of after-reaction of adding 1h, TLC (thin layer chromatography) monitoring the consumption of raw materials, the reaction liquid stirring slowly poured into 100 ml ice water, separating white solid, filtering, the filter cake is washed with saturated NaHCO3pH8 to, drying shall 10.2g white solid, that is, 2-nitro-terephthalic acid dimethyl ester (compound II), as shown in Figure 1, the yield 82.9percent

Molecular Weight:239.18
XLogP3:1.6
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:239.04298701
Monoisotopic Mass:239.04298701
Topological Polar Surface Area:98.4
Heavy Atom Count:17
Complexity:323
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes