Condensation of 3,3,3-trichloropropene with aromatic compounds

Summary

• 1. A study was made of the condensation of 3,3,3-trichloropropene with bromobenzene, chlorobenzene, and anisole, and the following previously unknown compounds were isolated in the pure state: p-BrC₄H₄CH₂CH = OCl₂; p-ClC₆H₄CH₂CH = CCl₂; p-CH₃OC₆H₄CH₂CH = CCl₂.

• 2. It was found that, when 3,3,3-trichloropropene reacts with phenol in presence or absence of aluminum chloride, a mixture of HOC₄H₄CH₂CH = CCl₂ and p-HOC₂H₄CH₂CH = CCl₂ is formed. When the condensation is carried out with sodium phenoxide in an alcoholic medium, not only the above-mentioned ortho and para isomers are formed, but also the phenoxy derivative C₆H₂OCH₂CH = CCl₂.

• 3. It was shown that 1,1-dichloro-3-p-chlorophenylpropene and 3-p-bromophenyl-1,1-dichloropropene unite with chlorine with formation of p-ClC₆H₄CH₂CHCl·CCl₂ and p-BrC₆H₄CH₂CHClCCl₃.

• 4. A study was made of the hydrolysis of the following compounds by concentrated H₂SO₄; p-ClC₄H₄CH₂CH-CCl₂; p-BrC₆H₄CH₂CH-CCl₂; p-CH₂OC₆H₄CCH₂H=CCl₂ and C₆H₅CH₂CH=CCl₂. It was found that the first two compounds are converted smoothly into the corresponding halohydrocinnamic acids; the other two compounds are not only hydrolyzed at the dichlorovinyl group, but are also sulfonated in the benzene ring.