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

HRID 1977703노트

반응식

HRID 1977703 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 101302194-Chloro-α,α-dimethylbenzeneacetonitrile수율 90.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-15 °C

실험 절차

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 2 M 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)

후처리

  1. stirringstirred at −15° C. for one hour
  2. extractionThe aqueous solution is extracted with ether
  3. extractionThe organic 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

출처 및 근거

ORD 기록
ord-75179ce9c23f463f847dc63ccc33b3e8
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235754B1

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