Ethyl Bromide → alpha-Ethyl-alpha-(4-chlorophenyl)-4-hydroxy-benzylalcohol

HRID 1980399

反応式

HRID 1980399 の反応式
[CH2:1]([Mg]Br)[CH3:2].[Mg].C(Br)C.[Cl:9][C:10]1[CH:24]=[CH:23][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1.[Cl-].[NH4+]>CCOCC>[Cl:9][C:10]1[CH:24]=[CH:23][C:13]([C:14]([CH2:1][CH3:2])([OH:15])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1

参加物

7

反応物 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 1235044-Hydroxy-4'-chlorobenzophenoneHCID 5462224MagnesiumHCID 178418443HCID 178418443、化合物

生成物 1

HCID 14727318alpha-Ethyl-alpha-(4-chlorophenyl)-4-hydroxy-benzylalcohol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-10 °C

実験手順

To a solution of ethyl magnesium bromide prepared from 3.9 g. of magnesium turnings and 17.4 g. of ethyl bromide in 50 ml. of dry ether a solution of 9.3 g. of 4-chloro-4'-hydroxy-benzophenone in 40 ml. of dry ether is added dropwise, with stirring at -10° C., in nitrogen atmosphere. The reaction mixture is allowed to warm up to room temperature, stirred at this temperature for an additional half an hour, and is then poured onto a solution of ammonium chloride in ice water under cooling. The aqueous phase is extracted with ether, the ethereal phases are combined, washed to neutral with water, and dried over anhydrous magnesium sulfate. After filtering the solvent is distilled off in vacuo, the residue is decolored with charcoal in methanol, the solution is filtered, and the solvent is evaporated under reduced pressure. The crude mixture is crystallized from a mixture of benzene and ethyl acetate to yield 5.5 g. of the named compound, melting at 148° to 149° C.

後処理

  1. temperatureto warm up to room temperature
  2. stirringstirred at this temperature for an additional half an hour
  3. temperatureunder cooling
  4. extractionThe aqueous phase is extracted with ether
  5. washwashed to neutral with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering the solvent
  8. distillationis distilled off in vacuo
  9. filtrationthe solution is filtered
  10. customthe solvent is evaporated under reduced pressure
  11. customThe crude mixture is crystallized from a mixture of benzene and ethyl acetate
  12. customto yield 5.5 g

出典と根拠

ORDレコード
ord-53d61037ce724e43bc1c56f669641de6
出典データセット
uspto-grants-1985_04
特許番号
US04508926

関連ノート

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