Dimethyl Sulfoxide → (4-Vinylphenyl)acetonitrile

HRID 11973

반응식

HRID 11973 반응식
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1)=[CH2:2].CS(C)=O.[C-:15]#[N:16].[K+]>O>[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][C:15]#[N:16])=[CH:5][CH:4]=1)=[CH2:2]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 74126p-Vinylbenzyl chloride

생성물 1

HCID 3944539(4-Vinylphenyl)acetonitrile

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 22.2 g 4-vinyl benzylchloride (0.131 mol), 60 mL dimethylsulfoxide, and 12.8 g potassium cyanide (0.196 mol) was stirred at room temperature for 17 hours. The mixture was poured into 500 mL water and extracted several times with ethyl acetate. The combined organic layers were washed with brine and concentrated under vacuum. The crude red oil was purified by column chromatography on silica gel using 7/93 ethyl acetate/hexane to give 4-vinylbenzylcyanide, a yellow oil (18.03 g, 96%).

후처리

  1. extractionextracted several times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. concentrationconcentrated under vacuum
  4. customThe crude red oil was purified by column chromatography on silica gel using 7/93 ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-fedfeb7246d14800a6bb242376675b00
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098525B2

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