Methanol → Methyl 4-methyl-3-nitrobenzoate

HRID 1987317Notes

Reaction equation

HRID 1987317 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 73194-Methyl-3-nitrobenzoic acid

Product 1

HCID 81816Methyl 4-methyl-3-nitrobenzoateYield 98%

Conditions

Temperature
0 °C

Procedure

A solution of 4-methyl-3-nitrobenzoic acid (27.95 g, 154 mmol) in MeOH (550 mL) was treated with concentrated H2SO4 (10 mL, 188 mmol) and heated to reflux for 17 hours. The reaction was cooled and concentrated under reduced pressure. EtOAc (300 mL) and brine (400 mL) were added and the solution cooled to 0° C. 10N NaOH solution (40 mL) was slowly added until the acid content was neutralized and the solution basic. The organic phase was separated and the aqueous was then extracted with EtOAc (2×400 mL), and the combined organic phases dried (MgSO4), filtered, and concentrated under reduced pressure to give 4-Methyl-3-nitrobenzoic acid methyl ester as a white solid (29.37 g, 98%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated under reduced pressure
  5. additionEtOAc (300 mL) and brine (400 mL) were added
  6. addition10N NaOH solution (40 mL) was slowly added until the acid content
  7. customThe organic phase was separated
  8. extractionthe aqueous was then extracted with EtOAc (2×400 mL)
  9. dry with materialthe combined organic phases dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35fffba715f849a2af3cd796c2337e2c
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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