Water → 4-(1h-Benzimidazol-2-yl)benzoic acid

HRID 375540Notes

Reaction equation

HRID 375540 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1.O.[OH-].[Na+]>C1COCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 2328806Methyl 4-(1H-benzo[d]imidazol-2-yl)benzoate

Product 1

HCID 7594194-(1h-Benzimidazol-2-yl)benzoic acidYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(1H-benzimidazol-2-yl)benzoate (Step A) (2.63 g) is stirred in THF (50 mL) and water (10 mL) with sodium hydroxide (2.08 g) at reflux for 4 hours. The solvent is evaporated and the residue treated with 2N hydrochloric acid (100 mL). The resulting suspension is collected, washed with methanol/ethyl acetate and dried to give 2.52 g of the title compound as a white solid.

Workup

  1. customThe solvent is evaporated
  2. additionthe residue treated with 2N hydrochloric acid (100 mL)
  3. customThe resulting suspension is collected
  4. washwashed with methanol/ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-d6321a9b9f97403a91e05f81e8a9d4d6
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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