Methyl iodide → 4-Chloro-α,α-dimethylbenzeneacetonitrile

HRID 1458382ノート

反応式

HRID 1458382 の反応式
[Cl:1]C1C=CC(CC#N)=CC=1.C([N-:14][CH:15](C)C)(C)C.[Li+].IC.CCCC[CH2:25][CH2:26][CH3:27].O1CCCC1.[CH:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1.O>[Cl:1][C:33]1[CH:38]=[CH:37][C:36]([C:26]([CH3:25])([CH3:27])[C:15]#[N:14])=[CH:35][CH:34]=1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 2415824-Chlorobenzyl cyanideHCID 2724682Lithium diisopropylamideHCID 86600160Heptane tetrahydrofuran benzene

生成物 1

HCID 101302194-Chloro-α,α-dimethylbenzeneacetonitrile収率 90.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

A solution of (p-chlorophenyl)acetonitrile (30.32 g, 0.20 mol) in tetrahydrofuran is treated dropwise with lithium diisopropylamide (0.44 mol, 220 mL of a 2M solution in heptane/tetrahydrofuran/benzene) at -25° C. to -30° C. over 60 minutes under nitrogen, stirred at -15° C. for one hour, treated dropwise with a solution of iodomethane (62.45 g, 0.44 mol) in tetrahydrofuran at -15° C., stirred at -15° C. for one hour, and diluted with water. The aqueous solution is extracted with ether The organic extract is washed sequentially with water, 2N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain an oily residue. The residue is distilled to give the title product as a colorless oil (32.6 g, bp 89°-91° C./1 mm Hg, 90.7% yield).

後処理

  1. stirringstirred at -15° C. for one hour
  2. extractionThe aqueous solution is extracted with ether The
  3. extractionorganic extract
  4. washis washed sequentially with water, 2N hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain an oily residue
  8. distillationThe residue is distilled

出典と根拠

ORDレコード
ord-b1163cb644d04cccbd842eb64d1bec24
出典データセット
uspto-grants-1998_12
特許番号
US05849958

反応ノート

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