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

HRID 2390975Notes

Reaction equation

HRID 2390975 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]CCCC)=[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 57615037Butyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate

Product 1

HCID 219900803-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acidYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methanol (5 mL) solution of 5.00 g of butyl 3-(2-(1-benzothiophen-5-yl)ethoxy)propionate was added water (5 mL) solution of 1.10 g of potassium hydroxide, which was then stirred at room temperature for 2 hours. This reaction mixture was distilled off under reduced pressure, to which were added 30 mL of toluene and 30 mL of water. The pH was adjusted to 1.6 with 3.5 mL of 6 mol/L hydrochloric acid. The organic layer was separated, followed by distilling off the solvent under reduced pressure. Thereto were added 15 mL of toluene and 30 mL of cyclohexane. The precipitate was collected by filtration to provide 3.60 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 30 mL of toluene and 30 mL of water
  3. customThe organic layer was separated
  4. distillationby distilling off the solvent under reduced pressure
  5. additionThereto were added 15 mL of toluene and 30 mL of cyclohexane
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5d7fb145773749c9b01a34b94c619504
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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