Reaktion #48461

Reaktionsgleichung

2-bromopropanoic acid

carbon disulfide

1-butanethiol

hydrochloric acid

sodium hydroxide

→

title compound

Ausbeute 62.2%

2-{[(butylsulfanyl)carbonothioyl]sulfanyl}propanoic Acid

Ausbeute 62.2%

Lösungsmittel

Acetone

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwas continued for 15 min
2. 2
   workup.STIRRINGThe reaction was stirred overnight
3. 3
   SonstigeThe acetone was removed under reduced pressure
4. 4
   Extraktionthe remaining mixture was extracted with ether (400 mL)
5. 5
   WaschenThe extract was washed with water (2×100 mL), saturated sodium chloride solution (200 mL)
6. 6
   Trocknendried (sodium sulfate)
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe oily residue was crystallized by the addition of ice (500 g)
9. 9
   Filtrationthe crystals were collected by filtration
10. 10
    Waschenwashed with water (5×100 mL)
11. 11
    Sonstigedried in a vacuum oven at room temperature
12. 12
    workup.DISSOLUTIONThe resulting impure product was redissolved in ether (400 mL)
13. 13
    Extraktionextracted with saturated sodium bicarbonate (5×150 mL)
14. 14
    Extraktionextracted with ether (400 mL)
15. 15
    ExtraktionThe organic extract
16. 16
    Waschenwas washed with saturated sodium chloride (200 mL)
17. 17
    Trocknendried (sodium sulfate)
18. 18
    Sonstigeevaporated under reduced pressure
19. 19
    SonstigeThe residue was crystallized by the addition of ice (500 g)
20. 20
    Sonstigethe solid was collected
21. 21
    Waschenwashed with water (5×1 50 mL)
22. 22
    Sonstigedried in a vacuum oven

Vorschrift

Acetone (700 mL) and tetrapropylammonium bromide (5.58 g, 21.0 mmol) were added with stirring to a solution of sodium hydroxide (10.5 g, 0.263 mol) in water (36 mL), followed by 1-butanethiol (23.7 g, 0.263 mol). After 20 min, carbon disulfide (17 mL, 21.7 g, 0.285 mol) was added and stirring was continued for 15 min, after which 2-bromopropanoic acid (40.14 g, 0.263 mol) was added. The reaction was stirred overnight, then acidified to pH<1 with 2 M hydrochloric acid (100 mL). The acetone was removed under reduced pressure and the remaining mixture was extracted with ether (400 mL). The extract was washed with water (2×100 mL), saturated sodium chloride solution (200 mL), dried (sodium sulfate), and evaporated. The oily residue was crystallized by the addition of ice (500 g), the crystals were collected by filtration and washed with water (5×100 mL) and then dried in a vacuum oven at room temperature. The resulting impure product was redissolved in ether (400 mL) and extracted with saturated sodium bicarbonate (5×150 mL). The combined aqueous extracts were acidified to pH<1 with concentrated hydrochloric acid and extracted with ether (400 mL). The organic extract was washed with saturated sodium chloride (200 mL), dried (sodium sulfate), and evaporated under reduced pressure. The residue was crystallized by the addition of ice (500 g) and the solid was collected and washed with water (5×1 50 mL), then dried in a vacuum oven to give the title compound (15, R3=C4H9) as a yellow solid (39.0 g, 62%).

Quelle