تفاعل #48462

معادلة التفاعل

Dodecanethiol

sodium hydroxide

2-bromopropanoic acid

carbon disulfide

→

title compound

المردود 111.7%

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

المردود 111.7%

المذيبات

water

acetone

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر