Methanol → Methyl 5-hydroxy-2-nitrobenzoate

HRID 1917714Notes

Reaction equation

HRID 1917714 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:18]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:18])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 118825-Hydroxy-2-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 12922678Methyl 5-hydroxy-2-nitrobenzoateYield 98%

Procedure

To MeOH (125 mL) was added 5-hydroxy-2-nitrobenzoic acid (1.02 g, 5.6 mmol) followed by dropwise addition of thionyl chloride (˜4 mL) and the mixture heated at reflux overnight. The solution was cooled to room temperature, concentrated in vacuo, reconcentrated twice from MeOH, dissolved in EtOAc, washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo to give methyl 5-hydroxy-2-nitrobenzoate (1.09 g, 5.5 mmol, 98%). 1H NMR (300 MHz, DMSO-d6) δ 11.38 (s, 1H), 8.05 (d, 1H), 7.03 (d, 1H), 7.01 (s, 1H), 3.82 (s, 3H); LC-MS (ESI) m/z 196 (M−H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26ba625ab11048ccb6937c572fe7f45e
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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