반응 #1914826

반응 방정식

16-bromohexadecan-1-ol

HCl

sodium

NaOH

thiolacetic acid

→

desired product

수율 70.3%

16-Mercaptohexadecan-1-ol

수율 70.3%

용매

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONAfter completion of addition the reaction mixture
2. 2
   workup.STIRRINGAfter additional 10 min of stirring 3 ml
3. 3
   workup.ADDITIONwere added
4. 4
   온도The resulted mixture was refluxed for 15 hrs
5. 5
   온도to cool to RT
6. 6
   온도The reaction completion required additional 3 hr of reflux
7. 7
   기타Resulted
8. 8
   기타reaction mixture
9. 9
   온도was cooled with ice bath
10. 10
    workup.ADDITIONpoured
11. 11
    workup.STIRRINGwith stirring, into a vessel
12. 12
    추출extracted with 300 ml of ether
13. 13
    기타The organic layer was separated
14. 14
    세척washed with 3×150 ml of water, 150 ml of saturated NaCl aqueous solution
15. 15
    건조dried over sodium sulfate
16. 16
    기타After ether removal material
17. 17
    workup.DISSOLUTIONwas dissolved in minimum amount of dicloromethane
18. 18
    기타purified by silica gel chromatography (100% dicloromethane as eluent)

실험 절차

Under inert atmosphere 365 mg of sodium metal suspension (40% in mineral oil) were added dropwise to 20 ml of dry methanol at 0° C. After completion of addition the reaction mixture was stirred for 10 min at RT followed by addition of 0.45 ml (6.30 mmole) of thiolacetic acid. After additional 10 min of stirring 3 ml degassed methanolic solution of 1.0 gr (3.11 mmole) of 16-bromohexadecan-1-ol were added. The resulted mixture was refluxed for 15 hrs, allowed to cool to RT and 20 ml of degassed 1.0 M NaOH aqueous solution were injected. The reaction completion required additional 3 hr of reflux. 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 ether removal material was dissolved in minimum amount of dicloromethane and purified by silica gel chromatography (100% dicloromethane as eluent). 600 mg (70% yield) of the desired product were obtained.

출처