反应 #833542

反应方程式

16bromohexadecanoic acid

HCl

sodium

NaOH

thioacetic acid

→

desired product

收率 97.2%

16-Mercaptohexadecanoic acid

收率 97.2%

溶剂

methanol

反应条件

后处理

1. 1
   workup.ADDITIONAt the end of the addition reaction mixture
2. 2
   workup.STIRRINGAfter additional 10 min of stirring
3. 3
   workup.ADDITIONwere added
4. 4
   温度The resulted mixture was refluxed for 15 hrs
5. 5
   温度to cool to RT
6. 6
   温度Additional refluxing for 3 hrs
7. 7
   其他required for reaction completion
8. 8
   其他Resulted
9. 9
   其他reaction mixture
10. 10
    温度was cooled with ice bath
11. 11
    workup.ADDITIONpoured
12. 12
    workup.STIRRINGwith stirring, into a vessel
13. 13
    萃取extracted with 300 ml of ether
14. 14
    其他The organic layer was separated
15. 15
    洗涤washed with 3×150 ml of water, 150 ml of saturated NaCI aqueous solution
16. 16
    干燥dried over sodium sulfate
17. 17
    其他After removal of ether material
18. 18
    其他was purified by recrystallization from n-hexane
19. 19
    过滤filtering out
20. 20
    其他drying over high vacuum

实验过程

Under inert atmosphere 2.0 gr of sodium metal suspension (40% in mineral oil) were slowly added to 100 ml of dry methanol at 0° C. At the end of the addition reaction mixture was stirred for 10 min at RT and 1.75 ml (21.58 mmole) of thioacetic acid were added. After additional 10 min of stirring, 30 ml degassed methanolic solution of 6.1 gr (18.19 mmole) of 16bromohexadecanoic acid were added. The resulted mixture was refluxed for 15 hrs, after which, allowed to cool to RT and 50 ml of degassed 1.0 M NaOH aqueous solution were injected. Additional refluxing for 3 hrs required for reaction completion. Resulted reaction mixture was cooled with ice bath and poured, with stirring, into a vessel containing 200 ml of ice water. This mixture was titrated to pH=7 by 1.0 M HCl and extracted with 300 ml of ether. The organic layer was separated, washed with 3×150 ml of water, 150 ml of saturated NaCI aqueous solution and dried over sodium sulfate. After removal of ether material was purified by recrystallization from n-hexane, filtering out and drying over high vacuum. 5.1 gr (97% yield) of the desired product was obtained.

来源