反応 #4306

反応方程式

thiophenol

4-chloro-1-butanol

potassium carbonate

→

clear oil

収率 57.8%

4-(Phenylthio)-1-butanol

収率 57.8%

溶媒

dimethoxyethane

chloroform

反応条件

後処理

1. 1
   温度was heated overnight
2. 2
   ろ過The reaction mixture was filtered
3. 3
   その他solvent removed by rotary evaporator
4. 4
   その他The residue obtained
5. 5
   抽出extracted with 10% sodium hydroxide
6. 6
   乾燥The chloroform layer was dried
7. 7
   ろ過filtered
8. 8
   その他solvent removed
9. 9
   その他to give an oil which
10. 10
    その他crystallized to a white solid
11. 11
    workup.DISTILLATIONdistilled at 134°-140° C./0.55 mm
12. 12
    洗浄for elution
13. 13
    その他This gave a clear oil which
14. 14
    その他was dried at 80° C. overnight in vacuo

実験手順

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.

出典