Lithium hydroxide, monohydrate → 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylic acid

HRID 2074115Notes

Reaction equation

HRID 2074115 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[N:10]=[N:9]2)=[CH:5][CH:4]=1.O[Li].O>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[N:9]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12937510Ethyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 185250351-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a mixture of ethyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate (190.0 g, 0.73 mol) and MeOH/H2O (350 mL/100 mL) was added LiOH.H2O (42.0 g, 0.97 mol) in portions at 0° C. and the reaction mixture was stirred at room temperature overnight. The mixture was evaporated, the residue was diluted with water (250 mL), then extracted with Et2O (3×75 mL) to remove neutral impurities. The aqueous layer was adjusted to pH=3-4 with conc. HCl and the precipitate was filtered to afford the title compound (160 g, 94.0%) as a white solid.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with water (250 mL)
  3. extractionextracted with Et2O (3×75 mL)
  4. customto remove neutral impurities
  5. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-19901b1a53a84af3a316026df36f7f07
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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