Water → bis(3,4-dichlorophenyl)methanone

HRID 1111259ノート

反応式

HRID 1111259 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 94813,4-DichlorobenzotrifluorideHCID 6451240Aluminum(III) Chloride2 回HCID 21863594Toluene ethanol

生成物 1

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

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-63f0abb2ccd74a5dbb9856b339b515e3
出典データセット
uspto-grants-1990_12
特許番号
US04978798

反応ノート

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