Réaction #56393

Équation de réaction

Sodium

ethyl dichloroacetate

4-methylthiophenol

→

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

Rendement 68.0%

Solvants

diethyl ether

methanol

methanol

methanol

Conditions de réaction

Traitement

1. 1
   Températureto cool
2. 2
   Autrethe white precipitate obtained
3. 3
   Filtrationis filtered off
4. 4
   Concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
5. 5
   AutreThe oil obtained
6. 6
   Lavagewashed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time)
7. 7
   SéchageThe ethereal phase is dried over anhydrous sodium sulphate
8. 8
   Filtrationfiltered
9. 9
   workup.ADDITIONtreated with animal charcoal
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Mode opératoire

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.

Source