Methanol → Methyl 2-methyl-5-nitrobenzoate

HRID 1582252Notes

Reaction equation

HRID 1582252 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[CH3:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoateYield 99%

Procedure

A solution of 2-methyl-5-nitrobenzoic acid (1.51 g, 8.34 mmol) and H2SO4 (catalytic) in MeOH (20 mL) was heated at reflux for 17 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (40 mL), washed with saturated NaHCO3(aq) (30 mL), then dried (MgSO4) and concentrated in vacuo to give yellow crystals (1.62 g, 99%). 1H NMR (CDCl3) δ2.72 (s, 3H), 3.96 (s, 3H), 7.44 (d, 1H, J=8.7 Hz), 8.24 (dd, 1H, J=8.7, 2.7 Hz), 8.78 (d, 1H, J=2.7 Hz).

Workup

  1. temperatureat reflux for 17 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (40 mL)
  4. washwashed with saturated NaHCO3(aq) (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c06442c27a9466d8149aeb70857bbc2
Source dataset
uspto-grants-2004_05
Patent number
US06734191B2

Reaction notes

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