Water → bis(3,4-dichlorophenyl)methanone

HRID 1111259노트

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HRID 1111259 반응식
[Cl-:1].[Al+3].[Cl-:3].[Cl-].[Cl:5][C:6]1[CH:7]=[C:8]([C:13](F)(F)F)[CH:9]=[CH:10][C:11]=1[Cl:12].[OH2:17].C(O)C.[C:21]1(C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClC1C=CC=CC=1Cl>[Cl:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:13]([C:23]1[CH:24]=[CH:25][C:26]([Cl:1])=[C:21]([Cl:3])[CH:22]=1)=[O:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 94813,4-DichlorobenzotrifluorideHCID 6451240Aluminum(III) Chloride2회HCID 21863594Toluene ethanol

생성물 1

HCID 2760559bis(3,4-dichlorophenyl)methanone수율 80%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매2회

실험 절차

Aluminum chloride (16 g.) was slurried with 1,2-dichlorbenzene (40 ml.). A solution of 3,4-dichlorobenzotrifluoride (21.5 g.) in 1,2-dichlorobenzene (40 ml.) was added to the aluminum chloride slurry over 1.25 hours. The solution became dark red and viscous. The reaction mixture was stirred for 88 hours at room temperature and then heated to 70° C. for 6 hours. The reaction contents were poured into water and the aqueous portion was extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate and filtered. The solvents were removed on a rotary evaporator (methylene chloride) followed by a bulb-to-bulb distillation to remove most of the dichlorobenzene (85° C., 10 torr). Aqueous ethanol (U.S. Industrial Chemical Company, special denatured ethanol, 10% water added, 100 ml. total) was added to the reaction product and the contents of the flask were refluxed overnight. The solution was allowed to cool and the solid was collected and washed with ethanol to give a whitish solid (25.7 g., 80% yield). An analytical sample was obtained by recrystallization from ethanol/toluene (3.5-1) mp =144.

후처리

  1. temperatureheated to 70° C. for 6 hours
  2. customThe reaction contents
  3. extractionthe aqueous portion was extracted with methylene chloride
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvents were removed on a rotary evaporator (methylene chloride)
  7. distillationfollowed by a bulb-to-bulb distillation
  8. customto remove most of the dichlorobenzene (85° C., 10 torr)
  9. additionAqueous ethanol (U.S. Industrial Chemical Company, special denatured ethanol, 10% water added, 100 ml. total) was added to the reaction product
  10. temperaturethe contents of the flask were refluxed overnight
  11. temperatureto cool
  12. customthe solid was collected
  13. washwashed with ethanol
  14. customto give a whitish solid (25.7 g., 80% yield)

출처 및 근거

ORD 기록
ord-63f0abb2ccd74a5dbb9856b339b515e3
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04978798

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