Dimethyl Sulfide → 2-tert-Butyl-2-[(4-chlorophenoxy)methyl]oxirane

Participants

Reaction Steps

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.

Provenance & Evidence