Chloroacetyl chloride → 1-(5-Benzenesulfonyl-2-hydroxy-phenyl)-ethanone

HRID 2221300노트

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HRID 2221300 반응식
Cl[CH2:2][C:3](Cl)=[O:4].[C:6]1([S:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[C:6]1([S:12]([C:15]2[CH:20]=[CH:2][C:3]([OH:4])=[C:17]([C:18](=[O:21])[CH3:19])[CH:16]=2)(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 3438044-(Benzenesulfonyl)phenolHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 189877381-(5-Benzenesulfonyl-2-hydroxy-phenyl)-ethanone

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

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온도
130 °C

실험 절차

Chloroacetyl chloride (2.35 g; 0.030 mol) was added at 0° C. to a solution of 4-benzenesulfonyl-phenol (2.34 g; 0.010 mol) in carbon disulfide (50 mL). After 10 minutes at ambient temperature, aluminum trichloride was added in small portions. The reaction was heated at 130° C. under reflux, and the carbon disulfide was distilled, after which the reaction was heated at 180° C. for 45 minutes. After cooling to ambient temperature, the mixture was treated with 10% aqueous HCl (25 mL), extracted with ethyl acetate (100 mL×2), dried (Na2SO4) and concentrated in vacuo. The solid residue was purified by column chromatography on silica gel (hexane-ethyl acetate; 7:3) to give 1-(5-benzenesulfonyl-2-hydroxy-phenyl)-ethanone as a white solid (1.924 g; 70%). A sample was recrystallized from ethyl acetate-hexane: MS; (M)+ 276, m. p. 155.5-157.3° C.

후처리

  1. temperatureunder reflux
  2. distillationthe carbon disulfide was distilled
  3. temperatureafter which the reaction was heated at 180° C. for 45 minutes
  4. temperatureAfter cooling to ambient temperature
  5. additionthe mixture was treated with 10% aqueous HCl (25 mL)
  6. extractionextracted with ethyl acetate (100 mL×2)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe solid residue was purified by column chromatography on silica gel (hexane-ethyl acetate; 7:3)

출처 및 근거

ORD 기록
ord-20231828d7a849208938c67e56a856e7
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368567B2

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