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

HRID 1601437Notes

Reaction equation

HRID 1601437 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 a saturated 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 a saturated dichloromethane
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-07a8f378b30d45439d7c663952dafc75
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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