Methanol → Methyl 2-methyl-5-nitrobenzoate

HRID 1157898Notes

Reaction equation

HRID 1157898 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 73%

Procedure

A solution of 2-methyl-5-nitrobenzoic acid (1.91 g, 10.6 mmol) and H2SO4 (catalytic) in MeOH (25 mL) was heated at reflux for 16 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (50 mL), washed with saturated NaHCO3(aq) (2×40 mL), then dried (MgSO4), filtered, and concentrated in vacuo to give yellow crystals (1.50 g, 73%). 1H NMR (CDCl3) δ 2.72 (s, 3H), 3.96 (s, 3H), 7.44 (d, 1H, J=9.0 Hz), 8.24 (dd, 1H, J=9.0, 3.0 Hz), 8.78 (d, 1H, J=3.0 Hz).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  4. washwashed with saturated NaHCO3(aq) (2×40 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c95ba8dd6d74f93890d30a4fbf29b36
Source dataset
uspto-grants-2010_10
Patent number
US07807694B2

Reaction notes

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