Hydrochloric Acid → 2-(benzyloxy)-4-(1H-imidazol-1-yl)benzoic acid hydrochloride

HRID 454475Notes

Reaction equation

HRID 454475 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:18]=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:26]>O1CCOCC1.CO>[ClH:26].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:18]=[CH:17][C:12]=1[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66990349methyl 2-(benzyloxy)-4-(1H-imidazol-1-yl)benzoate

Product 1

HCID 669904362-(benzyloxy)-4-(1H-imidazol-1-yl)benzoic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (0.63 mL) was added to a solution mixture of the obtained methyl 2-(benzyloxy)-4-(1H-imidazol-1-yl)benzoate (0.13 g) in dioxane (0.65 mL) and methanol (0.65 mL), followed by stiffing at room temperature for 3 hours. Under ice-cooling, 6 mol/L hydrochloric acid (0.21 mL) was added to the reaction mixture, and the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the solid substance was collected by filtration. Dioxane (1 mL) and a 4 mol/L hydrogen chloride-dioxane solution (0.5 mL) were added to the obtained solid substance, followed by stirring at room temperature for 1 hour. The solid substance was collected from the reaction mixture by filtration to obtain 0.097 g of 2-(benzyloxy)-4-(1H-imidazol-1-yl)benzoic acid hydrochloride as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. customthe solvent was evaporated under reduced pressure
  3. additionWater was added to the obtained residue
  4. filtrationthe solid substance was collected by filtration
  5. additionDioxane (1 mL) and a 4 mol/L hydrogen chloride-dioxane solution (0.5 mL) were added to the obtained solid substance
  6. filtrationThe solid substance was collected from the reaction mixture by filtration

Sources & evidence

ORD record
ord-ebfd96c3e64948f4903204b5566ec691
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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