Methanol → Salicylic acid, 4-nitro-, methyl ester

HRID 1793633Notes

Reaction equation

HRID 1793633 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[OH:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 692664-Nitrosalicylic acid

Product 1

HCID 139539Salicylic acid, 4-nitro-, methyl ester

Procedure

To a MeOH solution (200 ml) of 2-hydroxy-4-nitro-benzoic acid (18 g) was added concentrated sulfuric acid. The resulting mixture was heated to reflux for 24 h. After it was cooled to rt, volatile was removed in vacuo. The residue was then partitioned between water and EtOAc. The EtOAc layer was washed with water (2×), NaHCO3 (sat.), NaCl (sat.), dried over Na2SO4 and concentrated. The crude product was purified on a silica gel column with 20% EtOAc in hexane to give 14.5 g of 2-hydroxy-4-nitro-benzoic acid methyl ester as a solid (M+: 197).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 24 h
  3. customvolatile was removed in vacuo
  4. customThe residue was then partitioned between water and EtOAc
  5. washThe EtOAc layer was washed with water (2×), NaHCO3 (sat.), NaCl (sat.)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified on a silica gel column with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-1912afb005594a808886ebd13ae297f1
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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