Methanol → 3-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acid

HRID 553218Notes

Reaction equation

HRID 553218 reaction equation
CO.[S:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([O:19]CCC)=[O:18])=[CH:11][C:6]=2[CH:5]=[CH:4]1.[OH-].[K+]>O>[S:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][C:6]=2[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 57615042Propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate

Product 1

HCID 219900803-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acidYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methanol (12 mL) solution of 12.0 g of propyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate was added water (12 mL) solution of 2.76 g of potassium hydroxide, which was then stirred at room temperature for 1.5 hours. This reaction mixture was distilled off under reduced pressure, to which were added 36 mL of toluene and 36 mL of water. The pH was adjusted to 1.9 with 8 mL of 6 mol/L hydrochloric acid. The organic layer was separated, followed by distilling off the solvent under reduced pressure. Thereto were added 12 mL of toluene and 24 mL of cyclohexane. The precipitate was collected by filtration to provide 8.91 g of 3-(2-(1-benzothiophen-5-yl)ethoxy)propionic acid as white solid form.

Workup

  1. distillationThis reaction mixture was distilled off under reduced pressure, to which
  2. additionwere added 36 mL of toluene and 36 mL of water
  3. customThe organic layer was separated
  4. distillationby distilling off the solvent under reduced pressure
  5. additionThereto were added 12 mL of toluene and 24 mL of cyclohexane
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7804e11c8c2a4ceb8b8b7d7d25872000
Source dataset
uspto-grants-2011_05
Patent number
US07951963B2

Reaction notes

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