2-Nitrophenol → 2-[(2-Methylprop-2-en-1-yl)oxy]aniline

HRID 132577

반응식

HRID 132577 반응식
Cl[CH2:2][C:3]([CH3:5])=[CH2:4].[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([O-])=O.C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCO.C1COCC1.O.ClCCl.C1(C)C=CC=CC=1.C(#N)C>[CH3:5][C:3](=[CH2:4])[CH2:2][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH2:6]

참가 물질

10

반응물 4

HCID 69472-NitrophenolHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate3회HCID 24489Sodium Dithionite2회

생성물 1

HCID 136173332-[(2-Methylprop-2-en-1-yl)oxy]aniline

시약·촉매·용매 5

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매HCID 18504229Ethanol tetrahydrofuran water용매

실험 절차

A mixture of 3-chloro-2-methyl-1-propene (5.43 g, 60 mmol), 2-nitrophenol (5.56 g, 40 mmol), potassium carbonate (11.05 g, 80 mmol), tetrabutylammonium hydrogen sulfate (0.271 g, 0.89 mmol) and acetonitrile (120 ml) was heated under reflux for 16 h. The mixture was portioned between toluene and aqueous potassium carbonate (5%), and the organic phase was dried and concentrated. The residue and sodium dithionite (13.9 g, 80 mmol) in EtOH-THF-H2O (2:1:1, 100 ml) was heated under reflux for 3 h and left over the weekend in the fridge. Then, additional sodium dithionite (7 g, 40 mmol) was added and the mixture was boiled for 2 h. The reaction mixture was portioned between dichloromethane and aqueous potassium carbonate (10%) and the organic layer was dried (Na2SO4). Concentrated of the solution gave the subtitle compound.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. temperatureunder reflux for 3 h
  6. waitleft over the weekend in the fridge
  7. dry with materialthe organic layer was dried (Na2SO4)
  8. concentrationConcentrated of the solution

출처 및 근거

ORD 기록
ord-e7de82bca38447afb4fcc31b33f67a17
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388020B2

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