Chloroacetone → 2-Acetylbenzo[b]thiophene

HRID 258397Notes

Reaction equation

HRID 258397 reaction equation
[S-2:1].[Na+].[Na+].[S].Cl[C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.Cl[CH2:15][C:16](=[O:18])[CH3:17].[OH-].[Na+]>O.C(OCC)C.CN1CCCC1=O>[C:16]([C:15]1[S:1][C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=1)(=[O:18])[CH3:17]

Participants

9

Reactant 5

HCID 6571ChloroacetoneHCID 69962-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 14804Sodium SulfideHCID 5362487Sulfur

Product 1

HCID 898052-Acetylbenzo[b]thiopheneYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a 200 ml four-necked flask, equipped with a stirrer, a thermometer and a reflux condenser, were added 11.7 g (150 m moles) of anhydrous sodium sulfide, 3.2 g (100 m moles) of sulfur and 100 ml of N-methylpyrrolidone, and the mixture was stirred at room temperature for one hour. To the reaction mixture was dropwise added 14.1 g (100 m moles) of 2-chlorobenzaldehyde, and the mixture was stirred at room temperature for 12 hours. To the reaction mixture, was dropwise added 11.1 g (120 m moles) of chloroacetone with cooling, and the reaction mixture was stirred at room temperature for 6 hours. After finishing the reaction, 100 ml of diethyl ether and 100 ml of water were added to the reaction mixture, and pH value of the aqueous layer was adjusted to higher than 11 with a sodium hydroxide aqueous solution, and extracted with diethyl ether. The diethyl ether extract was washed twice with water, and the diethyl ether layer was concentrated under a reduced pressure to obtain 13.0 g of 2-acetylbenzo[b]thiophene (yield 74%). Purity of the product was 95% as determined by gas chromatography.

Workup

  1. customTo a 200 ml four-necked flask, equipped with a stirrer
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. temperaturewith cooling
  4. stirringthe reaction mixture was stirred at room temperature for 6 hours
  5. additionwere added to the reaction mixture, and pH value of the aqueous layer
  6. extractionextracted with diethyl ether
  7. extractionThe diethyl ether extract
  8. washwas washed twice with water
  9. concentrationthe diethyl ether layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-179d3449452b4e688d453a963c17d666
Source dataset
uspto-grants-1993_11
Patent number
US05266705

Reaction notes

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