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

HRID 2390973Notes

Reaction equation

HRID 2390973 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-c934b61e15eb4e9caeb31e0c2185daa8
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

Loading…