1,1-Dichloro-2,2-diethoxyethane → Chloroketene diethylacetal

Participants

Reaction Steps

To a solution of dichloroacetaldehyde diethylacetal (25 g; 0.1336 mol) in 150 ml of THF cooled to 0° C. was added 17.99 g (0.16 mol) of potassium t-butoxide in 50 ml of THF. The ice-bath was removed, and the reaction mixture was allowed to reflux for 16 hr and cooled. The reaction mixture was filtered (through celite) and a pale yellow solution was concentrated in vacuo at 30° C. The residue was distilled to afford 18.1 g (90%) of 2-chloro-1,1-diethoxyethylene (Formula V: R3 =Cl; R4 =H; R5 =R6 =OC2H5), a colorless liquid, b.p. 70°-76° C./20-25 mm.

Provenance & Evidence