Chloroacetone → 2-Acetylbenzothiophene

HRID 258397노트

반응식

HRID 258397 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

HCID 898052-Acetylbenzothiophene수율 74%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-179d3449452b4e688d453a963c17d666
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05266705

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