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

HRID 637170Notes

Reaction equation

HRID 637170 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-35d786aead6b48b2bd0e4f60b4820dcc
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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