反応 #1914824

反応方程式

16-bromohexadecanoic acid

HCl

sodium

NaOH

thiolacetic acid

→

desired product

収率 97.2%

16-Mercaptohexadecanoic acid

収率 97.2%

溶媒

methanol

反応条件

後処理

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
   その他required for reaction completion
8. 8
   その他Resulted
9. 9
   その他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
    抽出extracted with 300 ml of ether
14. 14
    その他The organic layer was separated
15. 15
    洗浄washed with 3×150 ml of water, 150 ml of saturated NaCl aqueous solution
16. 16
    乾燥dried over sodium sulfate
17. 17
    その他After removal of ether material
18. 18
    その他was purified by recrystalization from n-hexane
19. 19
    ろ過filtering out
20. 20
    その他drying over high vacuum

実験手順

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 thiolacetic acid were added. After additional 10 min of stirring, 30 ml degassed methanolic solution of 6.1 gr (18.19 mmole) of 16-bromohexadecanoic 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 NaCl aqueous solution and dried over sodium sulfate. After removal of ether material was purified by recrystalization from n-hexane, filtering out and drying over high vacuum. 5.1 gr (97% yield) of the desired product were obtained.

出典