Sodium Hydroxide → 4-(1-methyl-1H-1,2,3-triazol-5-yl)benzoic acid

HRID 2196430Notes

Reaction equation

HRID 2196430 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[CH:5][N:4]=[N:3]1.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)=[CH:5][N:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68600114HCID 68600114, compound

Product 1

HCID 593550104-(1-methyl-1H-1,2,3-triazol-5-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-(1-methyl-1H-1,2,3-triazol-5-yl)benzoate (0.5 g, 2.30 mmol) and Sodium hydroxide (4.60 ml, 9.21 mmol, 2N aqueous solution) in tetrahydrofuran (THF) was heated at 70° C. for 1 hr. The organic layer was washed with H2O 3× and discarded. The combined aqueous layers were acidified with 2N HCl aqueous solution. The product precipitated and was filtered, rinsed with H2O and dried under vacuum to give 0.3 g (74%) as a tan solid. LC-MS (ES) m/z=204 (M+H)+.

Workup

  1. washThe organic layer was washed with H2O 3×
  2. customThe product precipitated
  3. filtrationwas filtered
  4. washrinsed with H2O
  5. customdried under vacuum
  6. customto give 0.3 g (74%) as a tan solid

Sources & evidence

ORD record
ord-39ea39273d5a4400988140e5c73f629b
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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