Réaction #48462

Équation de réaction

Dodecanethiol

sodium hydroxide

2-bromopropanoic acid

carbon disulfide

→

title compound

Rendement 111.7%

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

Rendement 111.7%

Solvants

water

acetone

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source