Methanol → 4-Methoxy-3,5-dinitrobenzoic acid

HRID 852533Notes

Reaction equation

HRID 852533 reaction equation
[OH-:1].[K+].Cl[C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:16]([O-:18])=[O:17].[CH3:19]O>O>[CH3:19][O:1][C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 83774-Chloro-3,5-dinitrobenzoic acidHCID 14797Potassium Hydroxide2×

Product 1

HCID 2916454-Methoxy-3,5-dinitrobenzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of KOH (1.12 g, 20 mmol, 1 equiv) in MeOH (20 ml) at 0° C. was added portionwise 4-chloro-3,5-dinitrobenzoic acid (D23) (4.93 g, 20 mmol, 1 equiv). The resulting mixture was refluxed for 1 h then cooled to room temperature. A second portion of KOH (1.12 g, 20 mmol, 1 equiv) was added and the mixture refluxed for 90 min, cooled to room temperature and diluted with H2O. The aqueous phase was acidified to pH 1 and extracted with AcOEt. The organic phase was dried over MgSO4 and concentrated in vacuo to give crude 4-methoxy-3,5-dinitro-benzoic acid (D24) (4.49 g, 93%) as a light brown solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. temperaturethe mixture refluxed for 90 min
  3. temperaturecooled to room temperature
  4. extractionextracted with AcOEt
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5983826bf1fa4794b588b739d5b207e9
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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