4-Toluenesulfonyl chloride → (Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

HRID 464030노트

반응식

HRID 464030 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:12])=[CH:4][CH:3]=1.[OH-:13].[K+].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][OH:12])=[CH:6][CH:7]=1.[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O-:23])(=[O:22])=[O:13])=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 13660260HCID 13660260, 화합물

생성물 1

HCID 131714350(Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

Dissolve 7.3 g (0.04 mole) of (Z)-4-(4-chlorophenyl)but-2-en-ol in 100 ml of anhydrous ether. Add 3.2 g (0.05 mole) of powdered 86% KOH. Stir and cool the mixture in ice bath while adding a solution of 8.4 g (0.044 mole) of p-toluenesulfonyl chloride in 50 ml of anhydrous ether. Slowly warm the reaction mixture to room temperature and stir at room temperature for 16 hours. Remove the solid by filtration. Wash the filtrate with saturated aqueous sodium bicarbonate, H2O. Dry, evaporate, and recrystallize from cyclohexane to yield the title compound.

후처리

  1. temperaturecool the mixture in ice bath
  2. stirringstir at room temperature for 16 hours
  3. customRemove the solid
  4. filtrationby filtration
  5. washWash the filtrate with saturated aqueous sodium bicarbonate, H2O
  6. customDry
  7. customevaporate
  8. customrecrystallize from cyclohexane

출처 및 근거

ORD 기록
ord-c561988f1b4741a29d719acbe2eb3f19
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04545995

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