Methanol → Methyl 2-(2-nitrophenyl)acetate

HRID 1372733Notes

Reaction equation

HRID 1372733 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:19]O>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:19])=[O:12])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 520464Methyl 2-(2-nitrophenyl)acetateYield 97%

Procedure

To (2-nitrophenyl)acetic acid (25.0 g, 0.14 mol) were added methanol (100 ml) and concentrated sulfuric acid (3.0 ml). The resulting mixture was heated under reflux for 10 hours. The reaction mixture was cooled to room temperature and then, distilled under reduced pressure to remove the solvent. The residue was dissolved in chloroform. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (2:1, v/v) eluate fractions, methyl (2-nitrophenyl)acetate (26.6 g, 97%) was obtained as a yellow oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 10 hours
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. dissolutionThe residue was dissolved in chloroform
  6. washThe resulting solution was washed with a saturated aqueous solution of sodium bicarbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (2:1

Sources & evidence

ORD record
ord-66b6d1ef49ae4e7a8187440341145f81
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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