Methanol → 2-methoxy-5-(4H-triazol-4-yl)benzoic acid

HRID 582081Notes

Reaction equation

HRID 582081 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]2[CH:17]=[N:16][N:15]=[N:14]2)=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].CO.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]2[CH:17]=[N:16][N:15]=[N:14]2)=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 18464913methyl 2-methoxy-5-(4H-triazol-4-yl)benzoate

Product 1

HCID 184644732-methoxy-5-(4H-triazol-4-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine methyl 2-methoxy-5-(4H-triazol-4-yl)benzoate (56 mmol) and methanol (200 mL) and water (50 mL). Add 1M aqueous solution of sodium hydroxide (62.5 mL, 62.5 mmol). Heat to reflux. After 8 hour, concentrate in vacuo to remove most of the solvent. Adjust the pH to about 1 to 2 using a 1M aqueous hydrochloric acid solution, extract with dichloromethane. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 2-methoxy-5-(4H-triazol-4-yl)benzoic acid.

Workup

  1. temperatureHeat to reflux
  2. concentrationconcentrate in vacuo
  3. customto remove most of the solvent
  4. extractionextract with dichloromethane
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-31127189b0334c44bc5ddf0e0baa4811
Source dataset
uspto-grants-1999_07
Patent number
US05922737

Reaction notes

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