Hydrochloric Acid → 2-Methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetic acid

HRID 241361Notes

Reaction equation

HRID 241361 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([C:15](=[O:28])[CH2:16][CH2:17][C:18]2[S:19][C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[C:22]=2[CH3:23])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].O.O.[OH-].[Li+].Cl>C(O)C>[CH3:1][C:2]1[CH:14]=[C:13]([C:15](=[O:28])[CH2:16][CH2:17][C:18]2[S:19][C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=3[C:22]=2[CH3:23])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66884017Ethyl 2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetate

Product 1

HCID 444664652-Methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetic acidYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetate in ethanol (2 mL)/water (1 mL) was added lithium hydroxide monohydrate (70 mg, 1.7 mmol). The mixture was heated under reflux for 1 hour, cooled at room temperature. After addition of ice, the resultant mixture was acidified with 1M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the titled compound as a pale yellow crystal (120 mg, 59%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. additionAfter addition of ice
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-68ce6f8b703842e2abe2215af376ec9a
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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