Lithium hydroxide, monohydrate → 2-Methyl-5-(1H-tetrazol-1-yl)benzoic Acid

HRID 323424Notes

Reaction equation

HRID 323424 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O.[OH-].[Li+]>O1CCCC1.O.C(OCC)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 18464615methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate

Product 1

HCID 184648012-Methyl-5-(1H-tetrazol-1-yl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Combine methyl 2-methyl-5-(1H-tetrazol-1-yl)benzoate (5.2 g, 23.9 mmol) and lithium hydroxide hydrate (2.0 g, 47.7 mmol) in tetrahydrofuran/water (50 mL/50 mL). Heat to reflux. After 2 hours, dilute with diethyl ether and separate the layers. Extract the aqueous layer three times with diethyl ether. Extract the combined diethyl ether layers three times with a 1 M sodium hydroxide solution (20 mL). Combine the aqueous layers, acidify with a 1 M aqueous hydrochloric acid solution (pH about 1) to give a solid. Collect the solid by filtration and recrystallize form water to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customseparate the layers
  3. extractionExtract the aqueous layer three times with diethyl ether
  4. extractionExtract the combined diethyl ether layers three times with a 1 M sodium hydroxide solution (20 mL)
  5. customto give a solid
  6. customCollect the solid
  7. filtrationby filtration
  8. customrecrystallize
  9. customform water

Sources & evidence

ORD record
ord-70172bdc20e64502bf15224ad1c6e6c5
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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