Реакция #56393

Уравнение реакции

Sodium

ethyl dichloroacetate

4-methylthiophenol

→

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

Выход 68.0%

Растворители

diethyl ether

methanol

methanol

methanol

Условия реакции

Обработка

1. 1
   Температураto cool
2. 2
   Другоеthe white precipitate obtained
3. 3
   Фильтрацияis filtered off
4. 4
   Концентрированиеthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
5. 5
   ДругоеThe oil obtained
6. 6
   Промывкаwashed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time)
7. 7
   СушкаThe ethereal phase is dried over anhydrous sodium sulphate
8. 8
   Фильтрацияfiltered
9. 9
   workup.ADDITIONtreated with animal charcoal
10. 10
    Фильтрацияfiltered
11. 11
    Концентрированиеconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Методика

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.

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