Sodium Hydroxide → 5-Chloro-2-[(2-chlorophenoxy)methyl]benzoic acid

HRID 660196Notes

Reaction equation

HRID 660196 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68865815Methyl 5-chloro-2-[(2-chlorophenoxy)methyl]benzoate

Product 1

HCID 688644305-Chloro-2-[(2-chlorophenoxy)methyl]benzoic acidYield 86.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-chloro-2-[(2-chlorophenoxy)methyl]benzoate (step 1, 103 mg, 0.33 mmol) in methanol (4 mL) and tetrahydrofuran (4 mL) was 2 N sodium hydroxide (1 mL) and the mixture was stirred at room temperature for 16 hours. After removal of solvent, the residue was diluted with water (5 mL) and the solution was acidified with 2 N hydrochloric acid. Precipitate was collected by filtration, washed with water and dried in vacuo to afford 85 mg (86%) of the title compound:

Workup

  1. customAfter removal of solvent
  2. additionthe residue was diluted with water (5 mL)
  3. filtrationPrecipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cc189bc1a20447da8c9cdd37afd65973
Source dataset
uspto-grants-2011_12
Patent number
US08084476B2

Reaction notes

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