Citric Acid → 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoic acid

HRID 2230614Notes

Reaction equation

HRID 2230614 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[N:15]2)=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].C(OCC)(=O)C.CCCCCC.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[N:15]2)=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 18464866methyl 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 184650502-methoxy-5-(1H-triazol-1-ylmethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine methyl 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoate (1.14 g, 4.61 mmol) and methanol/tetrahydrofuran (1/1, 30 mL). Add a 1 M aqueous solution of lithium hydroxide (15 mL, 15 mmol). After 4 hours, acidify the reaction mixture with a 10% aqueous citric acid solution, add water, and extract twice with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give 2-methoxy-5-(1H-triazol-1-ylmethyl)benzoic acid: Rf=0.09 (silica gel, ethyl acetate).

Workup

  1. extractionextract twice with ethyl acetate
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. customevaporate in vacuo

Sources & evidence

ORD record
ord-84789062ccfa4c8a895725ab4567eb0c
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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