1-Chloro-4-nitrobenzene → 1-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzene

HRID 444174

Reaktionsgleichung

Reaktionsgleichung von HRID 444174
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17](Cl)=[CH:16][CH:15]=1)([O-:13])=[O:12].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:17]2[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 952944-Methylphenethyl alcohol

Produkt 1

HCID 51429261-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzeneAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-methylphenyl)ethyl alcohol (VIII) (13.6 g, 0.1 mole), 4-nitrochlorobenzene (IX: X=Cl) (15.8 g, 0.1 mole), toluene (92 g), tetra-n-butylammonium bromide (3.2 g, 0.01 mole) and a 50% aqueous sodium hydroxide solution (24 g) was stirred vigorously at 50° to 60° C. for 5 hours. The organic layer was separated, washed with water two times and then concentrated in vacuo. By recrystallizing the crude product from 95% ethanol, 20.6 g (yield, 80%) of 4-[2-(4-methylphenyl)ethoxy]nitrobenzene (VI) were obtained as white crystals.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with water two times
  3. concentrationconcentrated in vacuo
  4. customBy recrystallizing the crude product from 95% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6a6f3fd7760e41baa196c10fefa12708
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04263219

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