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

Participants

Reaction Steps

A solution of 162 ml (2.2 mole) of dimethyl sulphide in 400 ml of absolute acetonitrile is added to a solution of 189 ml (2.0 mole) of dimethyl sulphate in 1,200 ml of absolute acetonitrile at room temperature. The reaction mixture is allowed to stir overnight at room temperature. Then 118.8 g (2.2 mole) of sodium methylate are added. The mixture is allowed to stir for 30 minutes and then a solution of 272 g (1.2 mole) of 1-(4-chlorophenoxy)-3,3-dimethyl-2-butanone in 600 ml of absolute acetonitrile is added dropwise within 30 minutes. The reaction mixture is allowed to stir overnight. It is then evaporated, and the residue is partitioned between water and ethyl acetate, the organic phase is separated off, washed twice with water and once with saturated sodium chloride solution, dried over sodium sulphate, evaporated and the residue is distilled in vacuo. 242.2 g (84% of theory) of 2-(4-chlorophenoxymethyl)-2-tert.-butyl-oxirane of boiling point 115° -22° C./0.003 mm Hg column and of melting point 50°-52° C. are obtained.

Provenance & Evidence