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

HRID 1018804ノート

反応式

HRID 1018804 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 into 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 mixutre; yield=74%; m.p.=64° C.

後処理

  1. custommeasured in the liquid state at −78° C.
  2. customare bubbled into 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 mixutre

出典と根拠

ORDレコード
ord-8d60e7d78c004558bd93730df4572b87
出典データセット
uspto-grants-2002_11
特許番号
US06482986B1

反応ノート

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