Реакция #48462

Уравнение реакции

Dodecanethiol

sodium hydroxide

2-bromopropanoic acid

carbon disulfide

→

title compound

Выход 111.7%

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

Выход 111.7%

Растворители

water

acetone

Условия реакции

Обработка

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

Методика

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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