Methanol → Methyl 2-methyl-5-nitrobenzoate

HRID 8954

Reaction equation

HRID 8954 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-7b31324e4f2c4d8182cec42303622a5d
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Linked notes

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