Uses
The presence of the nitro group contributes to its potential reactivity and polar nature, while the methyl ester group enhances its solubility in organic solvents. Methyl 3-methyl-4-nitrobenzoate is often used in organic synthesis and may serve as an intermediate in the production of various pharmaceuticals and agrochemicals.
Synthesis
Step 1. Synthesis of methyl 3-methyl-4-nitrobenzoate
3-Methyl-4-nitrobenzoic acid (30 g, 165.61 mmol) was dissolved in methanol (300 mL), stirred at 0°C and thionyl chloride (25 mL) was added slowly and dropwise. The reaction mixture was warmed to 80°C and stirring was continued for 1 hour. Upon completion of the reaction, the mixture was concentrated under reduced pressure to give the crude product. The crude product was dissolved in petroleum ether (100 mL) and filtered to give methyl 3-methyl-4-nitrobenzoate as a white solid (31 g, 96% yield).
Product Characterization:
LC/MS (ES, m/z): [M + H]+ 196.01
1H-NMR (300MHz, CD3Cl) δ 7.99-8.04 (m, 3H), 3.98 (s, 3H), 2.64 (s, 3H)
References
[1] Patent: US2012/277224, 2012, A1. Location in patent: Page/Page column 33
[2] Chemical Communications, 2012, vol. 48, # 94, p. 11558 - 11560
[3] Chemical Communications, 2007, # 5, p. 504 - 506
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4582 - 4589
[5] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1573 - 1585
