SIDE-CHAIN CHLORINATION OF AROMATIC COMPOUNDS IN THE VAPOUR PHASE

According to the literature, the ethoxy- and methoxy-benzyl chlorides are prepared by the action of phosphorus trichloride or thionyl chloride on the corresponding alcohols. Ethyl and methyl ethers of ortho, meta- and para-cresols on chlorination in the vapour phase have yielded these chlorides, the yield in the case of the ortho-compound being 60-65%, the meta and para compounds furnishing 25% and 30% respectively. Ortho-, meta- and para-xylenes yield 50-60% of the corresponding xylyl chlorides. The chloro derivatives of anisole and cineol were obtained for the first time by the vapour phase chlorina­tions. Sunlight favours these side-chain chlorinations. The vapour phase chlorination of ortho-, meta- and para- nitrotoluenes was not successful, although these chlorinations are known to proceed well in the liquid phase.