3,5-Dinitrobenzoic acid → Methyl 3,5-dinitrobenzoate

To 3,5-Dinitro-benzoic acid (Aldrich, 21.2 g, 100 mmol) was added SOCl2. The mixture was refluxed overnight. The excess SOCl2 was removed under reduced pressure. The residue was dissolved in 100 mL of MeOH, cooled in ice bath, and triethylamine (Aldrich, 21 mL, 150 mmol) was added slowly added. After the mixture was stirred at ambient temperature for 3 h, solvent was removed under reduced pressure. The residue was diluted with EtOAc and 1N HCl. The mixture was extracted 3× with EtOAc (100 mL). The organic layers were washed twice with a brine solution (100 μL), dried over Na2SO4. Removal of the solvent gave 22.0 g (97%) of product, which was pure enough for the next reaction. 1H NMR (400 MHz, DMSO-d6) δ 9.05 (t, J=2.1 Hz, 1H), 8.92 (d, J=2.1 Hz, 2H), 3.99 (s, 3H).

1. temperatureThe mixture was refluxed overnight
2. customThe excess SOCl2 was removed under reduced pressure
3. dissolutionThe residue was dissolved in 100 mL of MeOH
4. temperaturecooled in ice bath
5. additionadded
6. customsolvent was removed under reduced pressure
7. additionThe residue was diluted with EtOAc and 1N HCl
8. extractionThe mixture was extracted 3× with EtOAc (100 mL)
9. washThe organic layers were washed twice with a brine solution (100 μL)
10. dry with materialdried over Na2SO4
11. customRemoval of the solvent

ORD record

ord-926d076c657e43e5825866e14bba4d93

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601841B2