4-[1-(1-Imidazolyl)-butyl]-benzoic acid methyl ester → 4-[1-(1-Imidazolyl)-butyl]-benzoic acid

HRID 727842Notes

Reaction equation

HRID 727842 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1>Cl>[N:14]1([CH:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:19])=[O:2])=[CH:5][CH:6]=2)[CH2:11][CH2:12][CH3:13])[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

3

Reactant 1

HCID 145143744-[1-(1-Imidazolyl)-butyl]-benzoic acid methyl ester

Product 1

HCID 145143684-[1-(1-Imidazolyl)-butyl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

23 g of the ester of example 1 is refluxed in 200 ml of concentrated hydrochloric acid for 20 hours. After concentration by evaporation in a vacuum, the residue is dissolved in water and brought to pH 8 with 50% sodium hydroxide solution. Then it is adjusted to pH 5-6 with 1M hydrochloric acid and evaporated to dryness. The crystalline residue is boiled several times with ethyl acetate and filtered. After concentration by evaporation, 20 g of 4-[1-(1-imidazolyl)-butyl]-benzoic acid with a melting point of 171°-172° C. is obtained.

Workup

  1. concentrationAfter concentration
  2. customby evaporation in a vacuum
  3. dissolutionthe residue is dissolved in water
  4. customevaporated to dryness
  5. filtrationfiltered
  6. concentrationAfter concentration
  7. customby evaporation, 20 g of 4-[1-(1-imidazolyl)-butyl]-benzoic acid with a melting point of 171°-172° C.
  8. customis obtained

Sources & evidence

ORD record
ord-500fc82252e74c27a197681b055adeb0
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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