Methanol → 2-methoxy-5-(1H-tetrazol-1-yl)benzoic acid

HRID 582075Notes

Reaction equation

HRID 582075 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[N:16][N:15]=[N:14]2)=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].CO.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[N:16][N:15]=[N:14]2)=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 18464873methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate

Product 1

HCID 184644352-methoxy-5-(1H-tetrazol-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Alternately, combine methyl 2-methoxy-5-(1H-tetrazol-1-yl)benzoate (13.3 g, 56.8 mmol) and methanol (150 mL). Add 1M aqueous solution of sodium hydroxide (62.5 mL, 62.5 mmol). Heat to reflux. After 30 minutes, add methanol (50 mL) and water (50 mL) and continue the heat at reflux. After 1 hour, concentrate in vacuo to remove most of the solvent. Adjust the pH to about 1 to 2 using a 1M aqueous hydrochloric acid solution to give a solid. Collect the solid by filtration, rinse with water, and dry to give 2-methoxy-5-(1H-tetrazol-1-yl)benzoic acid.

Workup

  1. temperatureHeat to reflux
  2. temperatureheat
  3. temperatureat reflux
  4. waitAfter 1 hour
  5. concentrationconcentrate in vacuo
  6. customto remove most of the solvent
  7. customto give a solid
  8. customCollect the solid
  9. filtrationby filtration
  10. washrinse with water
  11. customdry

Sources & evidence

ORD record
ord-771e122c237c49f084e41cc5ee48c1b0
Source dataset
uspto-grants-1999_07
Patent number
US05922737

Reaction notes

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