Methanol → Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

HRID 851857Notes

Reaction equation

HRID 851857 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(=O)(=O)(O)O.[CH3:19]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120334-Hydroxy-3-nitrobenzoic acid

Product 1

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl esterYield 58%

Procedure

4-Hydroxy-3-nitrobenzoic acid (10.0 g, 54.6 mmol) was suspended in methanol (60 mL). After addition of conc. sulfuric acid (0.1 mL), the suspension was heated overnight under reflux. The methanol was distilled off under reduced pressure. The residue was dissolved in ethyl acetate (40 mL), washed successively with aqueous sodium hydrogen carbonate (20 mL×2) and saturated aqueous brine (20 mL), and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, to give 6.27 g (yield 58%) of the desired compound in the form of a pale brown crystalline product.

Workup

  1. temperaturethe suspension was heated overnight
  2. temperatureunder reflux
  3. distillationThe methanol was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (40 mL)
  5. washwashed successively with aqueous sodium hydrogen carbonate (20 mL×2) and saturated aqueous brine (20 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-038a1129d0814dcda40f9f7c16e7474b
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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