Methanol → Methyl 3-methyl-4-nitrobenzoate

HRID 1975439Notes

Reaction equation

HRID 1975439 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 (100 mL twice), and drying at 40° C. under vacuum, to afford 103 g (95%) of methyl 3-methyl-4-nitrobenzoate as a yellow solid; mp 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 (100 mL twice), and
  9. customdrying at 40° C. under vacuum

Sources & evidence

ORD record
ord-b6f0b06166f5404eb0b34a274e184ab2
Source dataset
uspto-grants-1994_02
Patent number
US05286740

Reaction notes

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