Реакция #1252887

Уравнение реакции

dimethyl sulphide

dimethyl sulphate

1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one

sodium methylate

→

2-(4-chlorophenoxy-methyl)-2tert.-butyl-oxirane

Выход 84.0%

Растворители

acetonitrile

acetonitrile

acetonitrile

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred for 30 minutes
2. 2
   workup.WAITThe reaction mixture was further stirred overnight
3. 3
   Концентрированиеwas then concentrated
4. 4
   Другоеthe residue was partitioned between water and ethyl acetate
5. 5
   ДругоеThe organic phase was separated off
6. 6
   Промывкаwashed twice with water and once with saturated sodium chloride solution
7. 7
   Сушкаdried over sodium sulphate
8. 8
   Концентрированиеconcentrated
9. 9
   workup.DISTILLATIONthe residue was distilled in vacuo

Методика

A solution of 162 ml (2.2 mols) of dimethyl sulphide in 400 ml of absolute acetonitrile was added to a solution of 189 ml (2.0 mols) of dimethyl sulphate in 1,200 ml of absolute acetonitrile at room temperature. The reaction mixture was stirred overnight at room temperature. 118.8 g (2.2 mols) of sodium methylate were thereafter added to the mixture. The mixture was stirred for 30 minutes, and a solution of 272 g (1.2 mols) of 1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one in 600 ml of absolute acetonitrile was added dropwise to it during the course of 30 minutes. The reaction mixture was further stirred overnight and was then concentrated, and the residue was partitioned between water and ethyl acetate. The organic phase was separated off, washed twice with water and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated, and the residue was distilled in vacuo. 242.4 g (84% of theory) of 2-(4-chlorophenoxy-methyl)-2tert.-butyl-oxirane of boiling point 115°-122° C./0.003 mm Hg and melting point 50°-52° C. were obtained.

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