Phenol → (3-Chloropropoxy)benzene

HRID 1082135

Reaktionsgleichung

Reaktionsgleichung von HRID 1082135
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][CH2:9][CH:10](Cl)[Cl:11].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:11][CH2:10][CH2:9][CH2:8][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 65731,1-DichloropropaneHCID 14798Sodium Hydroxide

Produkt 1

HCID 76917(3-Chloropropoxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysator

Versuchsvorschrift

A two-phase mixture of phenol (5 g, 53 mmol), dichloropropane (32 ml), tetrabutylammonium hydrogen sulphate (0.3 g, 1 mmol), and sodium hydroxide solution (25 ml, 3M) was refluxed for 3 h. The organic layer was separated, dried (MgSO4), washed through a plug of silica with dichloromethane (200 ml), and concentrated in vacuo. The residues were distilled to give the title compound as a colourless, viscous oil (8.0 g, 88%) bp 110° C. at 0.1 mm Hg. NMR (CDCl3, 250 MHz) δ=2.26 (2H,q,J=6 Hz), 3.77 (2H,t,J=6 Hz), 4.13 (2H,t,J=6 Hz), 6.90-7.00 (3H,m), 7.26-7.34 (2H,m).

Aufarbeitung

  1. temperaturewas refluxed for 3 h
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. washwashed through a plug of silica with dichloromethane (200 ml)
  5. concentrationconcentrated in vacuo
  6. distillationThe residues were distilled

Quellen und Nachweise

ORD-Eintrag
ord-ebfaa74472f44d1fb9da402fb33c622c
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589500

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