Phenol → Benzene, 1-(3-chloropropoxy)-4-(methylthio)-

HRID 26004

Reaktionsgleichung

Reaktionsgleichung von HRID 26004
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][Cl:16].C1(O)C=CC=CC=1>COCCOC>[Cl:16][CH2:15][CH2:14][CH2:13][O:9][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Komponenten

6

Edukt 4

HCID 996PhenolHCID 80061-Bromo-3-chloropropaneHCID 140864-(Methylthio)phenol2×HCID 24758Sodium hydride

Produkt 1

HCID 12928626Benzene, 1-(3-chloropropoxy)-4-(methylthio)-Ausbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(methylthio)phenol (10.0 g, 0.071 mole) in 150 ml. of 1,2-dimethoxyethane is added to a slurry of a 57% dispersion of sodium hydride (3.0 g., 0.071 mole) in mineral oil (previously washed with hexane to remove the mineral oil) in 100 ml. of 1,2-dimethoxyethane. After the initial reaction is complete, 1-bromo-3-chloropropane (12.63 g., 0.08 mole) is added in one portion. The resulting mixture is stirred and refluxed for a period of 68 hrs., cooled and then concentrated under reduced pressure. Residual material (oil) is dissolved in ether and washed with water. The ether solution (after drying over magnesium sulfate) is concentrated under reduced pressure to provide 14.6 g. of an oil containing approximately 25% starting phenol according to NMR spectra. Distillation of the oil under reduced pressure affords, after a forerun of 4-(methylmercapto)phenol, 5.0 g. (32% yield) of 1-chloro-3-[4-(methylthio)phenoxy]propane, b.p. 150°-152° C. at 27 mm Hg.

Aufarbeitung

  1. washpreviously washed with hexane
  2. customto remove the mineral oil) in 100 ml
  3. customAfter the initial reaction
  4. temperaturerefluxed for a period of 68 hrs
  5. temperature, cooled
  6. concentrationconcentrated under reduced pressure
  7. dissolutionResidual material (oil) is dissolved in ether
  8. washwashed with water
  9. concentrationThe ether solution (after drying over magnesium sulfate) is concentrated under reduced pressure
  10. customto provide 14.6 g
  11. additionof an oil containing approximately 25%
  12. distillationDistillation of the oil under reduced pressure
  13. customaffords

Quellen und Nachweise

ORD-Eintrag
ord-ef82afb4fb2e42d4ba1847aa4f491733
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04147805

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