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

HRID 429462Notes

Reaction equation

HRID 429462 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 1 M 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 1 M 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-a19e339b4864497ca608b086fde5a594
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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