Methanol → Methyl 3-methyl-4-nitrobenzoate

HRID 1198294Notes

Reaction equation

HRID 1198294 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.O.[CH3:19]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH3:19])=[O:6]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 183703-Methyl-4-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 260927Methyl 3-methyl-4-nitrobenzoateYield 95%

Procedure

To a stirred suspension of 3-methyl-4-nitrobenzoic acid (100 g, 0.55 mole) in methanol (400 ml) was added thionyl chloride (36 g, 0.30 mole), over a period of 1 hour (the temperature of the reaction mixture rising to about 35°-40° C.). The mixture was heated to reflux for 1.5 hours, then cooled to 50°-55° C. and maintained at this temperature for 30 minutes prior to cooling to ambient temperature. Water (100 ml) was added over 30 minutes, with cooling applied to maintain the temperature at 20°-25° C. Filtration was followed by washing of the solid with water (2×100 ml), and drying at 40° C. under vacuum, to afford 103 g (95%) of methyl 3-methyl-4-nitrobenzoate as a yellow solid; m.p. 83°-85° C.; NMR (250 MHz, CDCl3), 2.62 (s, 3H, ArCH3), 3.98 (s, 3H, CO2CH3), 8.01 (m, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturecooled to 50°-55° C.
  4. temperaturemaintained at this temperature for 30 minutes
  5. temperaturewith cooling
  6. temperatureto maintain the temperature at 20°-25° C
  7. filtrationFiltration
  8. washby washing of the solid with water (2×100 ml)
  9. customdrying at 40° C. under vacuum

Sources & evidence

ORD record
ord-8f727f5876bf4a0ebc46eb8c229dd3ac
Source dataset
uspto-grants-1994_01
Patent number
US05280125

Reaction notes

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