Methanol → (7-Chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzofuran-3-yl)acetic acid

HRID 591467Notes

Reaction equation

HRID 591467 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[C:13]([Cl:14])[C:8]=2[O:7][CH:6]=1.CO.[OH-].[Na+]>C1COCC1>[Cl:14][C:13]1[C:8]2[O:7][CH:6]=[C:5]([CH2:4][C:3]([OH:25])=[O:2])[C:9]=2[CH:10]=[CH:11][C:12]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 118667011Methyl(7-chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzofuran-3-yl)acetate

Product 1

HCID 89768195(7-Chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzofuran-3-yl)acetic acidYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(7-chloro-6-((2,4-dichlorobenzyl)oxy)-1-benzofuran-3-yl)acetate (218.9 mg), MeOH (2.0 mL) and THF (dry) (2.0 mL) was added 1N NaOH (1.643 mL) at room temperature. The mixture was stirred at room temperature for 2 h. The residue was concentrated. The residue was neutralized with 1N HCl, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The precipitate was collected by filtration, and crystallized from EtOH-hexane to give the title compound (184 mg).

Workup

  1. concentrationThe residue was concentrated
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe precipitate was collected by filtration
  7. customcrystallized from EtOH-hexane

Sources & evidence

ORD record
ord-84c93ce63f6846dcb6dc17b4e70d92c5
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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