Ethylene Glycol → Benzo[b]thiophene-5-acetic acid

HRID 553205Notes

Reaction equation

HRID 553205 reaction equation
C(O)CO.[S:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14](C(OCC)=O)[C:15]([O:17]CC)=[O:16])=[CH:13][C:8]=2[CH:7]=[CH:6]1.[OH-].[K+].O>C1(C)C=CC=CC=1>[S:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][C:15]([OH:17])=[O:16])=[CH:13][C:8]=2[CH:7]=[CH:6]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 14797Potassium HydroxideHCID 57615034HCID 57615034, compound

Product 1

HCID 11469582Benzo[b]thiophene-5-acetic acidYield 12.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To ethylene glycol (11.0 mL) suspension of 0.25 g of diethyl 2-(1-benzothiophen-5-yl)malonate were added 11.0 mL of 40% (w/w) potassium hydroxide aqueous solution and 0.3 mL of water, which was then refluxed for 2 hours. To the reaction mixture were added water and toluene, and the aqueous layer was separated. The pH was adjusted to 2 with 6 mol/L hydrochloric acid, and thereto was added ethyl acetate. The organic layer was separated, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was suspended to 5 mL of xylene, and thereto was added 0.01 g of p-toluenesulfonic acid monohydrate, which was then refluxed for 30 minutes. The solvent was distilled off under reduced pressure, and to the resultant residue were added toluene and cyclohexane. The precipitate was collected by filtration to provide 0.02 g of 2-(1-benzothiophen-5-yl)acetic acid as pale yellow solid form.

Workup

  1. temperaturewas then refluxed for 2 hours
  2. customthe aqueous layer was separated
  3. additionwas added ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. additionwas added 0.01 g of p-toluenesulfonic acid monohydrate, which
  8. temperaturewas then refluxed for 30 minutes
  9. distillationThe solvent was distilled off under reduced pressure
  10. additionto the resultant residue were added toluene and cyclohexane
  11. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c2d6c2e590fc4829a9ac181d653cd1dc
Source dataset
uspto-grants-2011_05
Patent number
US07951963B2

Reaction notes

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