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

HRID 1052911Notes

Reaction equation

HRID 1052911 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-595b2afae4034afeb53319b3f0ca9a97
Source dataset
uspto-grants-2016_07
Patent number
US09388145B2

Reaction notes

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