Chlorine → 1-[3-Chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

HRID 1071918ノート

反応式

HRID 1071918 の反応式
[Cl-:1].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:23])[CH2:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)[CH2:7]1.ClCl>ClCCl>[Cl:1][C:15]1[CH:16]=[C:17]([C:20](=[O:22])[CH3:21])[CH:18]=[CH:19][C:14]=1[CH:8]1[CH2:7][C:6]([CH3:23])([CH3:5])[CH2:11][C:10]([CH3:12])([CH3:13])[CH2:9]1

参加物

5

反応物 3

HCID 24526ChlorineHCID 6451240Aluminum(III) ChlorideHCID 223904281-[4-(3,3,5,5-Tetramethylcyclohexyl)phenyl]ethanone

生成物 1

HCID 223904251-[3-Chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

40.25 g of aluminium chloride are added at 0° C., under an inert atmosphere, to 350 ml of dichloromethane, followed by addition of 5 g of 1-[4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (compound V.1) dissolved in dichloromethane. After stirring for 2 hours at 0° C., 17.1 ml of chlorine gas (d=1.565, measured in the liquid state at −78° C.) are bubbled through the reaction. After warming to room temperature, a water/ice mixture is added to the reaction mixture. The resulting mixture is extracted with dichloromethane, the phases are separated after settling has taken place, and the organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The residue is purified on a column of silica gel, eluting with a 7/3 (v/v) cyclohexane/dichloromethane mixture; yield=74%; m.p.=64° C.

後処理

  1. custommeasured in the liquid state at −78° C.
  2. customare bubbled through the reaction
  3. temperatureAfter warming to room temperature
  4. additiona water/ice mixture is added to the reaction mixture
  5. extractionThe resulting mixture is extracted with dichloromethane
  6. customthe phases are separated after settling
  7. dry with materialthe organic phase is dried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified on a column of silica gel
  10. washeluting with a 7/3 (v/v) cyclohexane/dichloromethane mixture

出典と根拠

ORDレコード
ord-e85f22dd83f24d5bb8b05512111f2a22
出典データセット
uspto-grants-2005_06
特許番号
US06908914B1

反応ノート

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