Methanol → Methyl 2-methyl-4-nitrobenzoate

HRID 2375871Notes

Reaction equation

HRID 2375871 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:19]O>>[CH3:19][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:7]=1[CH3:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 747904-Nitro-o-toluic acid

Product 1

HCID 15088700Methyl 2-methyl-4-nitrobenzoate

Conditions

Temperature
55 °C

Procedure

H2SO4 (98%, 0.030 mL) was added dropwise into the MeOH (30 mL) solution of 2-methyl-4-nitrobenzoic acid at rt. The mixture was then heated at 55° C. After 50 h, the solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O (25 mL each). The aqueous layer was extracted with another portion of EtOAc (25 mL). The combined extracts were washed with saturated NaHCO3 (25 mL), H2O (2×25 mL), and brine (25 mL), dried over MgSO4, filtered and concentrated in vacuo to give the title compound as light-yellow solid. 1H NMR (CDCl3, 400 MHz): δ=2.69 (s, 3H), 3.95 (s, 3H), 8.03-8.12 (m, 3H). MS (ES+): m/z 196.25 (100) [MH+]. HPLC: tR=3.29 min (ZQ2000, polar—5 min).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and H2O (25 mL each)
  3. extractionThe aqueous layer was extracted with another portion of EtOAc (25 mL)
  4. washThe combined extracts were washed with saturated NaHCO3 (25 mL), H2O (2×25 mL), and brine (25 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63cf5fec6a1b46148ed0cbe006510cab
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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