Water → 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

HRID 38508

Reaktionsgleichung

Reaktionsgleichung von HRID 38508
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[OH-].[K+].O.Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[Cl:22]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[Cl:22][C:14]1[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=1[O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 74431,2-Dichloro-4-nitrobenzeneHCID 11474PiconolHCID 14797Potassium Hydroxide

Produkt 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridineAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of pyridin-2-ylmethanol (6.82 g, 62.5 mmol), Aliquat 336 (8.08 g, 20.0 mmol), potassium hydroxide (3.51 g, 62.5 mmol) and water (40 mL) were added toluene (80 mL) and 1,2-dichloro-4-nitrobenzene (10.0 g, 52.1 mmol). The mixture was heated to 60° C. overnight with vigorous stirring. The layers were separated, and the organic layer was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The residue was triturated with petroleum ether and tert-butyl methyl ether to yield 6.66 g (48%) of the title compound.

Aufarbeitung

  1. customThe layers were separated
  2. additionthe organic layer was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was triturated with petroleum ether and tert-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-15de7fde64bc4f4184ec232e0020d2d1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524722B2

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