Hydrochloric Acid → 2,4-Dichloro-5-(pyridin-2-yl)benzoic acid

HRID 522138Notes

Reaction equation

HRID 522138 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-].O.Cl>>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 118497036Methyl 2,4-dichloro-5-(pyridin-2-yl)benzoate

Product 1

HCID 1184970902,4-Dichloro-5-(pyridin-2-yl)benzoic acidYield 100.2%

Procedure

To a solution of methyl 2,4-dichloro-5-(pyridin-2-yl)benzoate (Preparation 44, 3.96 g, 14 mmol) in industrial methylated spirit (60 mL) was added a 2M solution of LiOH in water (35 mL, 70 mmol) and the reaction was stirred at room temperature for 3 hours. The reaction was acidified with 2M HCl (aq) (35 mL) to afford a white precipitate that was filtered and washed with industrial methylated spirit to afford the title compound (3.76 g, quant.).

Workup

  1. customto afford a white precipitate that
  2. filtrationwas filtered
  3. washwashed with industrial methylated spirit

Sources & evidence

ORD record
ord-5a59f012b0954591a16afe5d98825084
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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