Potassium Carbonate → 1-(5-Hydroxy-1-benzothiophen-2-yl)ethan-1-one

HRID 2183624

Reaction equation

HRID 2183624 reaction equation
C(O[C:10]1[C:18]2[CH:17]=[C:16]([C:19](=[O:21])[CH3:20])[S:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-:23].[K+].[K+].[OH-].[Na+]>O1CCCC1>[OH:23][C:11]1[CH:12]=[CH:13][C:14]2[S:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][C:18]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 224736702-Acetylbenzo[b]thiophen-4-yl benzoate

Product 1

HCID 122356811-(5-Hydroxy-1-benzothiophen-2-yl)ethan-1-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-acetylbenzo[b]thiophen-4-yl benzoate (0.13 g), potassium carbonate (0.18 g), tetrahydrofuran (25 ml) and 5M aqueous sodium hydroxide solution (10 ml) was heated under reflux for 1 hour, then cooled to ambient temperature and concentrated in vacuo. The aqueous residue was acidified by the addition of 5M hydrochloric acid (20 ml), then the product was extracted into dichloromethane (2×25 ml). The combined extracts were washed with water (20 ml), 10% aqueous sodium hydrogencarbonate solution (3×20 ml) and water (2×20 ml), then dried (MgSO4) and the solvent was removed in vacuo to give 1-(5-hydroxybenzo[b]thiophen-2-yl]ethan-1-one (0.07 g) as a yellow solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. concentrationconcentrated in vacuo
  4. additionThe aqueous residue was acidified by the addition of 5M hydrochloric acid (20 ml)
  5. extractionthe product was extracted into dichloromethane (2×25 ml)
  6. washThe combined extracts were washed with water (20 ml), 10% aqueous sodium hydrogencarbonate solution (3×20 ml) and water (2×20 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-742a1357f62c4f90931c5e1fa0a986ca
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Linked notes

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