Sodium Hydroxide → (6-((2,4-Dichlorobenzyl)oxy)-4-methyl-1-benzothiophen-3-yl)acetic acid

HRID 591395Notes

Reaction equation

HRID 591395 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[C:9]2[C:10]([CH3:24])=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[CH:13][C:8]=2[S:7][CH:6]=1.[OH-].[Na+]>CCO>[Cl:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[CH2:15][O:14][C:12]1[CH:11]=[C:10]([CH3:24])[C:9]2[C:5]([CH2:4][C:3]([OH:25])=[O:2])=[CH:6][S:7][C:8]=2[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118667001Methyl(6-((2,4-dichlorobenzyl)oxy)-4-methyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 118656147(6-((2,4-Dichlorobenzyl)oxy)-4-methyl-1-benzothiophen-3-yl)acetic acidYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl(6-((2,4-dichlorobenzyl)oxy)-4-methyl-1-benzothiophen-3-yl)acetate (200 mg) and EtOH (2 mL) was added 1N NaOH (1 mL) at room temperature, and the mixture was refluxed for 15 min. The solution was cooled and concentrated under reduced pressure. The residue was neutralized with 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed successively with 1N HCl and brine, dried over MgSO4, and the mixture was concentrated in vacuo. The residue was crystallized from EtOAc to give the title compound (164 mg).

Workup

  1. temperaturethe mixture was refluxed for 15 min
  2. temperatureThe solution was cooled
  3. concentrationconcentrated under reduced pressure
  4. customwas neutralized with 1N HCl at 0° C.
  5. extractionextracted with EtOAc
  6. customThe organic layer was separated
  7. washwashed successively with 1N HCl and brine
  8. dry with materialdried over MgSO4
  9. concentrationthe mixture was concentrated in vacuo
  10. customThe residue was crystallized from EtOAc

Sources & evidence

ORD record
ord-6a33bd4fa9124258aff4f0c53c048234
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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