反应 #48462

反应方程式

Dodecanethiol

sodium hydroxide

2-bromopropanoic acid

carbon disulfide

→

title compound

收率 111.7%

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

收率 111.7%

溶剂

water

acetone

反应条件

后处理

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

实验过程

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%).

来源