Acetyl chloride → 1-((1,1'-Biphenyl)-3-yl)ethan-1-one

HRID 918027

反応式

HRID 918027 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Mg:14].[C:15](Cl)(=[O:17])[CH3:16].[Cl-].[NH4+]>C(OCC)C.O.O.[Cl-].[Cd+2].[Cl-].O>[CH:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C-:2][CH:3]=2)=[CH:9][CH:10]=1.[Mg+2:14].[Br-:1].[C:8]1([C:4]2[CH:3]=[C:2]([C:15](=[O:17])[CH3:16])[CH:7]=[CH:6][CH:5]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

9

反応物 4

HCID 6367Acetyl chlorideHCID 164493-BromobiphenylHCID 25517Ammonium ChlorideHCID 5462224Magnesium

生成物 2

HCID 2585681-((1,1'-Biphenyl)-3-yl)ethan-1-one収率 69.6%HCID 15971951Magnesium bromide 1,1'-biphenyl (1/1/1)

試薬・触媒・溶媒 3

HCID 53471205Cadmium(2+);dichloride;dihydrate触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒4 回

反応条件

温度
12 °C

実験手順

3-Biphenylmagnesium bromide was prepared according to known procedures from 100 g of 3-bromobiphenyl and 10 g of magnesium turnings in diethyl ether. To the Grignard reagent solution at 4°C was added 40 g of cadmium chloride dihydrate over a 1-hour period. The reaction mixture was heated at reflux for one hour and cooled to 12°C. To the reaction mixture then was added a solution of 32 g of acetyl chloride in diethyl ether over a period of 30 minutes. The reaction mixture was heated at reflux for 30 minutes, allowed to cool to room temperature, and agitated overnight. Additional diethyl ether was added and the reaction mixture again was heated at reflux for one hour. The reaction mixture was cooled and successively treated with 100 ml of saturated aqueous ammonium chloride and 100 ml of water. The reaction mixture was poured over ice, the diethyl ether layer which formed was separated, and the aqueous layer was extracted with diethyl ether. The diethyl ether layer and extracts were combined, washed successively with water until the wash water was neutral to litmus paper, and dried over anhydrous sodium sulfate. The diethyl ether was evaporated and the residue was vacuum distilled to give 29.3 g of 3'-phenylacetophenone, bp 12°C/0.3 mm. The following elemental analysis was obtained:

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for one hour
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 30 minutes
  5. temperatureto cool to room temperature
  6. temperaturethe reaction mixture again was heated
  7. temperatureat reflux for one hour
  8. temperatureThe reaction mixture was cooled
  9. additionThe reaction mixture was poured over ice
  10. customwas separated
  11. extractionthe aqueous layer was extracted with diethyl ether
  12. washwashed successively with water until the wash water
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe diethyl ether was evaporated
  15. distillationdistilled

出典と根拠

ORDレコード
ord-9110783b6e814cd3a3eea737eb4b9587
出典データセット
uspto-grants-1976_07
特許番号
US03968251

関連ノート

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