Methanol → 3-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1747220Notes

Reaction equation

HRID 1747220 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]1[C:5]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#N.C[OH:18]>O>[CH3:3][C:4]1[C:5]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]([OH:18])=[O:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67086543HCID 67086543, compound

Product 1

HCID 670868833-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4M aq. NaOH (10 mL, 40.2 mmol) was added to a RT solution of 3-methyl-2-(2H-1,2,3-triazol-2-yl)benzonitrile (1.48 g, 8.04 mmol) in MeOH (15 mL) and the resulting mixture was heated to 90° C. for 50 h. The reaction mixture was cooled to RT and diluted with water before the organic solvent was removed in vacuo. The remaining aqueous phase was acidified with 1M aq. HCl and extracted with EtOAc (3×). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the title compound that was used further without purification. LC-MS B: tR=0.50 min; [M+H]+=186.17.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customwas removed in vacuo
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-21c247bd30b04f5ba5a4f3652175f13b
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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