Hydrochloric Acid → 4-[3-(3-Benzyloxy-2-pyridyl)propyl)benzoic acid

HRID 2395075Notes

Reaction equation

HRID 2395075 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:15][CH2:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CCO>[CH2:1]([O:8][C:9]1[C:10]([CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18974026Methyl 4-[3-(3-benzyloxy-2-pyridyl)propyl)benzoate

Product 1

HCID 189738664-[3-(3-Benzyloxy-2-pyridyl)propyl)benzoic acidYield 18.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-[3-(3-benzyloxy-2-pyridyl)propyl)benzoate (0.3 g, 0.83 mmol) was dissolved in EtOH (3 ml) and treated with 1N NaOH (1.66 ml). The reaction was stirred at ambient temperature for 18 hours. A solution of hydrochloric acid (1N, 1.66 ml) was added and the resulting precipitate was filted and recrystallised from ethanol to give the title product as a white solid (0.054 g).

Workup

  1. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-7a57372d50a043baac58aa0b5ce95450
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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