Hydrochloric Acid → 4-(1-Imidazolyl)benzoic Acid

HRID 247592

Reaction equation

HRID 247592 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.[OH-].[Na+].O>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoate

Product 1

HCID 7365294-(1-Imidazolyl)benzoic Acid

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Combine methyl 4-fluorobenzoate (1.52 g, 10 mmol), 1H-imidazole (0.82g, 12 mmol) and potassium carbonate (1.40 g, 10 mmol) in dimethylsulfoxide (7 mL) and heat the mixture with stirring at 120°-130° C. for 5 hours, cool, add water and acid, extract with ether. Adjust the pH of the aqueous layer to 8 with sodium carbonate, extract with ether, dry the extract with sodium sulfate and evaporate. 4-(1H-Imidazol -1-yl)benzoic acid is prepared by refluxing this methyl ester (0.61 g, 3 mmol) in 5 mL of 10% aqueous sodium hydroxide for five minutes; cool, neutralize to pH 6-7 with hydrochloric acid, filter and dry the precipitated acid.

Workup

  1. temperaturecool
  2. extractionextract with ether
  3. extractionextract with ether
  4. customdry the
  5. extractionextract with sodium sulfate
  6. customevaporate
  7. filtrationfilter
  8. customdry the precipitated acid

Sources & evidence

ORD record
ord-1da2c005a2d8428ba59bce9b6c23a38f
Source dataset
uspto-grants-1987_11
Patent number
US04709043

Linked notes

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