반응 #1914824

반응 방정식

16-bromohexadecanoic acid

HCl

sodium

NaOH

thiolacetic acid

→

desired product

수율 97.2%

16-Mercaptohexadecanoic acid

수율 97.2%

용매

methanol

반응 조건

후처리

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
   온도The resulted mixture was refluxed for 15 hrs
5. 5
   온도to cool to RT
6. 6
   온도Additional refluxing for 3 hrs
7. 7
   기타required for reaction completion
8. 8
   기타Resulted
9. 9
   기타reaction mixture
10. 10
    온도was cooled with ice bath
11. 11
    workup.ADDITIONpoured
12. 12
    workup.STIRRINGwith stirring, into a vessel
13. 13
    추출extracted with 300 ml of ether
14. 14
    기타The organic layer was separated
15. 15
    세척washed with 3×150 ml of water, 150 ml of saturated NaCl aqueous solution
16. 16
    건조dried over sodium sulfate
17. 17
    기타After removal of ether material
18. 18
    기타was purified by recrystalization from n-hexane
19. 19
    여과filtering out
20. 20
    기타drying over high vacuum

실험 절차

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.

출처