Hydrochloric Acid → 4-(2H-triazol-4-yloxy)butanoic acid

HRID 870616Notes

Reaction equation

HRID 870616 reaction equation
[OH-].[Na+].[N:3]1[NH:4][N:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])[CH:7]=1.Cl>C(O)C>[N:3]1[NH:4][N:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86726579methyl 4-(2H-triazol-4-yloxy)butanoate

Product 1

HCID 867265814-(2H-triazol-4-yloxy)butanoic acidYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Add 1N sodium hydroxide (2.32 mL; 2.0 equiv; 2.32 mmoles) to a solution of methyl 4-(2H-triazol-4-yloxy)butanoate (0.215 g; 1.0 equiv; 1.16 mmoles) in ethanol (1 mL) and heat the mixture to 60° C. for 16 hours. Add 1N hydrochloric acid (2.32 mL; 2.0 equiv; 2.32 mmoles) and concentrate to afford 4-(2H-triazol-4-yloxy)butanoic acid (0.20 g; 100%). Use without further purification in the next step: MS (m/z): 170(M−1).

Workup

  1. concentrationconcentrate

Sources & evidence

ORD record
ord-22cbbcf9c8a9473da21557204933a111
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

Loading…