Hydrochloric Acid → 2-methoxy-5-(5-trifluoromethyl-1H-tetrazol-1-yl)benzoic acid

HRID 1584509Notes

Reaction equation

HRID 1584509 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]([F:21])([F:20])[F:19])=[N:16][N:15]=[N:14]2)=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]([F:21])([F:19])[F:20])=[N:16][N:15]=[N:14]2)=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18464579methyl 2-methoxy-5-(5-trifluoromethyl-1H-tetrazol-1-yl)benzoate

Product 1

HCID 184646042-methoxy-5-(5-trifluoromethyl-1H-tetrazol-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Combine methyl 2-methoxy-5-(5-trifluoromethyl-1H-tetrazol-1-yl)benzoate (1.46 g, 5.27 mmol) and an aqueous solution of sodium hydroxide (20 mL, 2M, 40 mmol) in methanol/tetrahydrofuran (20 mL/10 mL). After 2 hours, adjust the pH of the reaction mixture to about 2 using a 1M aqueous hydrochloric acid solution. Extract the reaction mixture with ethyl acetate and then dichloromethane. Dry the combined organic layers over MgSO4, filter, and evaporate in vacuo to give a the title compound: Rf =0.55 (silica gel, 85% chloroform/10% methanol/5% acetic acid).

Workup

  1. extractionExtract the reaction mixture with ethyl acetate
  2. dry with materialDry the combined organic layers over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo

Sources & evidence

ORD record
ord-8281152a485a4c9199efc94856a29c26
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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