Sulfuric Acid → 1-[(2,2-Dichloroethenyl)oxy]-3-methylbenzene

Participants

Reaction Conditions

Reaction Steps

By an electrochemical reductive dehydrohalogenation method. 1(3-tolyloxy)-2,2,2-trichloroethyl acetate (15.8 g), concentrated sulphuric acid (98% w/v, 9.8 g) and methanol (220 ml) was charged into an electrolytic cell, which was surrounded by a cooling bath set to maintain the temperature at about 15° C, and fitted with a cylindrical diaphragm, stirrer, reference electrode (SCE) and a working electrode. The cathode was a lead plate (surface area about 40 cm2). Using a current density in the range 5 to 10 mA/cm2 the reaction was conducted in the potential range -1100 to 1700 mV (SCE). When reduction was completed the cathodic electrolyte was neutralised with caustic soda and extracted with methylene chloride, the extracts dried over anhydrous sodium sulphate and evaporated to yield a residue of crude 3-tolyl 2,2-dichlorovinyl ether.

Provenance & Evidence