The chemistry of acetylenic ethers XI: Preparation of acetylenic ethers from aldehydes

A method for the preparation of acetylenic ethers starting from aldehydes I is described. The aldehydes are transformed into α‐chloroethers II and these are halogenated to α,β‐dihalogeno‐ethers III. By means of diethylaniline a molecule of hydrogen halide is eliminated, yielding a β‐halogeno‐α,β‐unsaturated ether IV. From this a second molecule of hydrogen halide can be eliminated by heating with potassium hydroxide, resulting in the formation of an acetylenic ether V.