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

HRID 591472Notes

Reaction equation

HRID 591472 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[C:9]2[C:10]([CH3:25])=[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]([CH3:14])[C:8]=2[O:7][CH:6]=1.CO.[OH-].[Na+]>C1COCC1>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:12]1[CH:11]=[C:10]([CH3:25])[C:9]2[C:5]([CH2:4][C:3]([OH:26])=[O:2])=[CH:6][O:7][C:8]=2[C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 71721635Methyl(6-((2,4-dichlorobenzyl)oxy)-4,7-dimethyl-1-benzofuran-3-yl)acetate

Product 1

HCID 89768061(6-((2,4-Dichlorobenzyl)oxy)-4,7-dimethyl-1-benzofuran-3-yl)acetic acidYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(6-((2,4-dichlorobenzyl)oxy)-4,7-dimethyl-1-benzofuran-3-yl)acetate (147 mg), MeOH (2.0 mL) and THF (dry) (2.0 mL) was added 1N NaOH (1.12 mL) at room temperature. The mixture was stirred at room temperature for 2 h, and then concentrated in vacuo. The residue was neutralized with 1N HCl, and the mixture was extracted with EtOAc. The organic layer was washed with brine and, dried over MgSO4, and concentrated in vacuo. The precipitate was collected by filtration, and crystallized from EtOAc-hexane to give the title compound (118 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionthe mixture was extracted with EtOAc
  3. washThe 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 EtOAc-hexane

Sources & evidence

ORD record
ord-7ca562ccaeaa456b87eb5a4a0031fedf
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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