Ethanol → 1-Hydroxy-1H-1,2,3-triazole-4-carboxylic Acid

HRID 2045143Notes

Reaction equation

HRID 2045143 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][N:9]([OH:11])[CH:10]=1)=[O:5])C.CCO.O.[OH-].[Li+]>O>[OH:11][N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[N:8]1

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 5270538Ethyl 1-hydroxy-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 534331041-Hydroxy-1H-1,2,3-triazole-4-carboxylic AcidYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Hydroxy-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (2.0 g, 13 mmol) and EtOH (25 mL) were combined with a pre-dissolved solution of lithium hydroxide monohydrate (1.6 g, 38.2 mmol) and water (10 mL), and stirred at room temperature for 4 hours. The mixture was partially concentrated and acidified with HCl to cause precipitation. The solid was filtered and dried under vacuum to yield the title compound (1.3 g).

Workup

  1. concentrationThe mixture was partially concentrated
  2. customprecipitation
  3. filtrationThe solid was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d06c5fb256e44da595cd33457ae84bbf
Source dataset
uspto-grants-2013_11
Patent number
US08586536B2

Reaction notes

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