1-Phenyl-1-propanol → (1-Chloropropyl)benzene

HRID 529182

반응식

HRID 529182 반응식
[C:1]1([CH:7](O)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.CS([Cl:24])(=O)=O>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:24][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][CH3:9]

참가 물질

6

반응물 3

HCID 71471-Phenyl-1-propanolHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

생성물 1

HCID 524241(1-Chloropropyl)benzene수율 54%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

Under ice cooling, to a solution of 1-phenyl-1-propanol (1.0 g, 7.34 mmol) and N-ethyldiisopropylamine (1.42 g, 11.01 mmol) in dichloromethane (10 ml) was added methanesulfonyl chloride (690 μl, 8.81 mmol), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent:ethyl acetate/hexane:5/1) to give 1-chloro-1-phenylpropane (610 mg, 54%) as pale yellow liquid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate, and solvent
  4. distillationwas distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography (eluent:ethyl acetate/hexane:5/1)

출처 및 근거

ORD 기록
ord-8d609fad395f47b2b33f5039c244650c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346822B2

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