Reacción #56393

Ecuación de reacción

Sodium

ethyl dichloroacetate

4-methylthiophenol

→

Ethyl 2,2-bis(4-methylthiophenoxy)acetate

Rendimiento 68.0%

Disolventes

diethyl ether

methanol

methanol

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool
2. 2
   Otrothe white precipitate obtained
3. 3
   Filtraciónis filtered off
4. 4
   Concentraciónthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
5. 5
   OtroThe oil obtained
6. 6
   Lavadowashed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time)
7. 7
   SecadoThe ethereal phase is dried over anhydrous sodium sulphate
8. 8
   Filtraciónfiltered
9. 9
   workup.ADDITIONtreated with animal charcoal
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Procedimiento

Sodium (3.54 g) is dissolved in methanol (140 cc) and a solution of 4-methylthiophenol (21.8 g) in methanol (25 cc) is added. The mixture is stirred for 1 hour at 20° C. and a solution of ethyl dichloroacetate (12.5 g) in methanol (30 cc) is then added. The mixture is allowed to cool, the white precipitate obtained is filtered off, and the filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C. The oil obtained is taken up in diethyl ether (250 cc) and washed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time). The ethereal phase is dried over anhydrous sodium sulphate, filtered, treated with animal charcoal, filtered and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methylthiophenoxy)acetate (18 g) is thus obtained as a yellow oil.

Fuente