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

HRID 132577

反応式

HRID 132577 の反応式
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]

参加物

10

反応物 4

HCID 69472-NitrophenolHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate3 回HCID 24489Sodium Dithionite2 回

生成物 1

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

試薬・触媒・溶媒 5

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 18504229Ethanol tetrahydrofuran water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e7de82bca38447afb4fcc31b33f67a17
出典データセット
uspto-grants-2008_06
特許番号
US07388020B2

関連ノート

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