Reaktion #4306

Reaktionsgleichung

thiophenol

4-chloro-1-butanol

potassium carbonate

→

clear oil

Ausbeute 57.8%

4-(Phenylthio)-1-butanol

Ausbeute 57.8%

Lösungsmittel

dimethoxyethane

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated overnight
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Sonstigesolvent removed by rotary evaporator
4. 4
   SonstigeThe residue obtained
5. 5
   Extraktionextracted with 10% sodium hydroxide
6. 6
   TrocknenThe chloroform layer was dried
7. 7
   Filtrationfiltered
8. 8
   Sonstigesolvent removed
9. 9
   Sonstigeto give an oil which
10. 10
    Sonstigecrystallized to a white solid
11. 11
    workup.DISTILLATIONdistilled at 134°-140° C./0.55 mm
12. 12
    Waschenfor elution
13. 13
    SonstigeThis gave a clear oil which
14. 14
    Sonstigewas dried at 80° C. overnight in vacuo

Vorschrift

A mixture of thiophenol (121.2 g, 1.10 mole), 4-chloro-1-butanol (100.0 g, 0.921 mole), and potassium carbonate (138.2 g, 1.0 mole) was heated overnight at gentle reflux in dimethoxyethane. The reaction mixture was filtered and solvent removed by rotary evaporator. The residue obtained was dissolved in chloroform and extracted with 10% sodium hydroxide. The chloroform layer was dried, filtered, and solvent removed to give an oil which crystallized to a white solid. The solid was vacuum distilled at 134°-140° C./0.55 mm. A six-gram sample of the distilled oil was subjected to flash chromatography on silica gel using ethyl acetate-hexanes for elution. This gave a clear oil which was dried at 80° C. overnight in vacuo. The process produced 5.2 g (57.8%) of clear oil.

Quelle