반응 #48462

반응 방정식

Dodecanethiol

sodium hydroxide

2-bromopropanoic acid

carbon disulfide

→

title compound

수율 111.7%

2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid

수율 111.7%

용매

water

acetone

반응 조건

후처리

1. 1
   온도The resulting solution was cooled in an ice bath
2. 2
   기타The solution was evaporated
3. 3
   workup.ADDITIONfurther diluted with water (150 mL)
4. 4
   기타The resulting solid was collected
5. 5
   기타recrystallised from ether/light petroleum

실험 절차

Dodecanethiol (2.50 g, 12.5 mmol), acetone (40 mL), and tetrapropylammonium bromide (0.27 g, 0.10 mmol) were added to a solution of sodium hydroxide (0.50 g, 12.5 mmol) in water (5 mL). The resulting solution was cooled in an ice bath and treated with carbon disulfide (0.75 mL, 0.95 g, 12.5 mmol). After 20 min, 2-bromopropanoic acid (1.91 g, 12.5 mmol) was added and the mixture was stirred at ambient temperature for 12 h. The solution was evaporated to ¼ volume and slowly acidified with 2 M hydrochloric acid (50 mL), then further diluted with water (150 mL). The resulting solid was collected and recrystallised from ether/light petroleum to give the title compound (15, R3=C12H25) as yellow crystals (3.33 g, 76%).

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