Реакция #1914824

Уравнение реакции

16-bromohexadecanoic acid

HCl

sodium

NaOH

thiolacetic acid

→

desired product

Выход 97.2%

16-Mercaptohexadecanoic acid

Выход 97.2%

Растворители

methanol

Условия реакции

Обработка

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
   ТемператураThe resulted mixture was refluxed for 15 hrs
5. 5
   Температураto cool to RT
6. 6
   ТемператураAdditional refluxing for 3 hrs
7. 7
   Другоеrequired for reaction completion
8. 8
   ДругоеResulted
9. 9
   Другоеreaction mixture
10. 10
    Температураwas cooled with ice bath
11. 11
    workup.ADDITIONpoured
12. 12
    workup.STIRRINGwith stirring, into a vessel
13. 13
    Экстракцияextracted with 300 ml of ether
14. 14
    ДругоеThe organic layer was separated
15. 15
    Промывкаwashed with 3×150 ml of water, 150 ml of saturated NaCl aqueous solution
16. 16
    Сушкаdried over sodium sulfate
17. 17
    ДругоеAfter removal of ether material
18. 18
    Другоеwas purified by recrystalization from n-hexane
19. 19
    Фильтрацияfiltering out
20. 20
    Другоеdrying over high vacuum

Методика

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.

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