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

HRID 1193088Notes

Reaction equation

HRID 1193088 reaction equation
[CH3:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#N.[OH-:15].[Na+].C[OH:18]>O>[CH3:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([OH:18])=[O:15]

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

To a solution of 3-methyl-2-(2H-1,2,3-triazol-2-yl)benzonitrile (1.4 g, 7.82 mmol) in MeOH (15 mL) was added a 4N aqueous solution of NaOH (10 mL). The resulting mixture was heated to 90° C. After 15 h the reaction mixture was cooled to ambient temperature then diluted with water (50 mL). The aqueous layer was acidified to pH2 and extracted with EtOAc (50 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated.

Workup

  1. temperatureAfter 15 h the reaction mixture was cooled to ambient temperature
  2. extractionextracted with EtOAc (50 mL) three times
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8449263808a54a5f9fea5e7a6e7676fa
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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