반응 #4306

반응 방정식

thiophenol

4-chloro-1-butanol

potassium carbonate

→

clear oil

수율 57.8%

4-(Phenylthio)-1-butanol

수율 57.8%

용매

dimethoxyethane

chloroform

반응 조건

후처리

1. 1
   온도was heated overnight
2. 2
   여과The reaction mixture was filtered
3. 3
   기타solvent removed by rotary evaporator
4. 4
   기타The residue obtained
5. 5
   추출extracted with 10% sodium hydroxide
6. 6
   건조The chloroform layer was dried
7. 7
   여과filtered
8. 8
   기타solvent removed
9. 9
   기타to give an oil which
10. 10
    기타crystallized to a white solid
11. 11
    workup.DISTILLATIONdistilled at 134°-140° C./0.55 mm
12. 12
    세척for elution
13. 13
    기타This gave a clear oil which
14. 14
    기타was dried at 80° C. overnight in vacuo

실험 절차

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.

출처