Reaktion #217463

Reaktionsgleichung

16-bromohexadecanoic acid

HCl

sodium

NaOH

thiolacetic acid

→

desired product

Ausbeute 97.2%

16-Mercaptohexadecanoic acid

Ausbeute 97.2%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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
   TemperaturThe resulted mixture was refluxed for 15 hrs
5. 5
   Temperaturto cool to RT
6. 6
   TemperaturAdditional refluxing for 3 hrs
7. 7
   Sonstigerequired for reaction completion
8. 8
   SonstigeResulted
9. 9
   Sonstigereaction mixture
10. 10
    Temperaturwas cooled with ice bath
11. 11
    workup.ADDITIONpoured
12. 12
    workup.STIRRINGwith stirring, into a vessel
13. 13
    Extraktionextracted with 300 ml of ether
14. 14
    SonstigeThe organic layer was separated
15. 15
    Waschenwashed with 3×150 ml of water, 150 ml of saturated NaCl aqueous solution
16. 16
    Trocknendried over sodium sulfate
17. 17
    SonstigeAfter removal of ether material
18. 18
    Sonstigewas purified by recrystallization from n-hexane
19. 19
    Filtrationfiltering out
20. 20
    Sonstigedrying over high vacuum

Vorschrift

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 recrystallization from n-hexane, filtering out and drying over high vacuum. 5.1 gr (97% yield) of the desired product were obtained.

Quelle