Water → Ethyl 5-hydroxy-2-(5-methyltetrazol-1-yl)benzoate

HRID 2383163Notes

Reaction equation

HRID 2383163 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]([N:16]2[C:20]([CH3:21])=[N:19][N:18]=[N:17]2)=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)C.[O-]CC.[K+].O.[Cl-].[NH4+]>CN(C=O)C>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([N:16]2[C:20]([CH3:21])=[N:19][N:18]=[N:17]2)=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23670592Potassium ethoxideHCID 67051123Ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoate

Product 1

HCID 67050952Ethyl 5-hydroxy-2-(5-methyltetrazol-1-yl)benzoateYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoate (164 g, 0.565 mol) was dissolved in 500 mL of DMF and immersed in a water bath. Potassium ethoxide (52.3 g, 0.621 mol) was added to this solution portionwise, keeping the reaction temperature below 40° C. After 30 minutes, the reaction was poured into 4 L of water and ammonium chloride was added to the solution until the product precipitated. After one hour of stirring, the precipitate was filtered and dried under a flow of air to give 98.5 g of ethyl 5-hydroxy-2-(5-methyltetrazol-1-yl)benzoate as a white solid.

Workup

  1. customimmersed in a water bath
  2. customthe reaction temperature below 40° C
  3. additionwas added to the solution until the product
  4. customprecipitated
  5. filtrationthe precipitate was filtered
  6. customdried under a flow of air

Sources & evidence

ORD record
ord-2ecfdd2ea9784e1697c1f2cd9912bea2
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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