3,5-Dinitrobenzoic acid → 3-Methoxy-5-nitrobenzoic acid

Temperature

80 °C

3,5-Dinitrobenzoic acid (866 mg) was dissolved in 1 M LiOMe in MeOH (1.3 mL), then evaporated to dryness. The resulting solid was dissolved in 30 mL of hexamethyl phosphoramide and heated at 80° C. for 16 h. The mixture was then cooled and poured onto a mixture of crushed ice (250 g) and 6NH2SO4 (42 mL). The mixture was extracted with ether, and the extract was washed with water and brine, then dried over MgSO4, filtered and evaporated to yield an orange solid. Filtration through silica gel using 9:1 CH2Cl2/MeOH followed by evaporation provided 624 mg of product. 1H-NMR (d6-acetone): δ 8.36 (1H, dd, J=1.6, 2.0 Hz), 7.97 (1H, t, J=2.0 Hz), 7.91 (1H, dd, J=1.6, 2.0 Hz), 4.03 (3H, s).

1. customevaporated to dryness
2. dissolutionThe resulting solid was dissolved in 30 mL of hexamethyl phosphoramide
3. temperatureThe mixture was then cooled
4. additionpoured onto a mixture of crushed ice (250 g) and 6NH2SO4 (42 mL)
5. extractionThe mixture was extracted with ether
6. washthe extract was washed with water and brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customevaporated
10. customto yield an orange solid
11. filtrationFiltration through silica gel using 9:1 CH2Cl2/MeOH
12. customfollowed by evaporation

ORD record

ord-716e8cc2f07245f58fe8715f93c2f019

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855192B2