Reacción #48462

Ecuación de reacción

Dodecanethiol

sodium hydroxide

2-bromopropanoic acid

carbon disulfide

→

title compound

Rendimiento 111.7%

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

Rendimiento 111.7%

Disolventes

water

acetone

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente