Lithium Hydroxide → 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoic acid

HRID 2230611Notes

Reaction equation

HRID 2230611 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Li+]>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18465024methyl 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoate

Product 1

HCID 184645852-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine methyl 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoate (0.45 g, 1.73 mmol) and methanol/tetrahydrofuran (1/1, 10 mL). Add a 1 M aqueous solution of lithium hydroxide (5.8 mL, 5.8 mmol). After 4 hours, partition the reaction mixture between water and ethyl acetate. Acidify the aqueous with a 10% aqueous citric acid solution, extract four times with ethyl acetate, combine the ethyl acetate layers, dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoic acid: Rf=0.60 (silica gel, 1/1 methanol/dichloromethane).

Workup

  1. custompartition the reaction mixture between water and ethyl acetate
  2. extractionextract four times with ethyl acetate
  3. dry with materialdry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-32d3222fe0484df79fbbc678a7acd941
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

Loading…