Reaction #56393

Reaction equation

Sodium

ethyl dichloroacetate

4-methylthiophenol

→

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

Yield 68.0%

Solvents

diethyl ether

methanol

methanol

methanol

Conditions

Workup

1. 1
   Temperatureto cool
2. 2
   Otherthe 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
   OtherThe oil obtained
6. 6
   Washwashed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time)
7. 7
   DryingThe 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

Procedure

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