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

Participants

Reaction Steps

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 mL), 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).

Provenance & Evidence