Lithium Hydroxide → 3-(1H-tetrazol-1-yl)benzoic acid

HRID 2230628Notes

Reaction equation

HRID 2230628 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([O:11]CC)=[O:10])[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Li+]>O1CCCC1.O>[N:1]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([OH:11])=[O:10])[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18464674ethyl 3-(1H-tetrazol-1-yl)benzoate

Product 1

HCID 7502203-(1H-tetrazol-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Combine ethyl 3-(1H-tetrazol-1-yl)benzoate (4.93 g, 22.6 mmol) and tetrahydrofuran/water (100 mL/25 mL). Add lithium hydroxide (1.9 g, 45.2 mmol) and heat to reflux. After 2 hours, cool to ambient temperature and extract the reaction mixture five times with a 1 M aqueous sodium hydroxide solution. Combine the aqueous layers and extract with ethyl acetate. Acidify the aqueous layers with a 1 M aqueous hydrochloric acid solution (pH about 1) to give a solid. Collect the solid by filtration to give the title compound.

Workup

  1. extractionextract the reaction mixture five times with a 1 M aqueous sodium hydroxide solution
  2. extractionextract with ethyl acetate
  3. customto give a solid
  4. customCollect the solid
  5. filtrationby filtration

Sources & evidence

ORD record
ord-fb5589c2fd294a4689a73f602d7e9bca
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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