Hydrolysis of polyhalohydrocarbons containing the CHal₃ or CCl₂=CH group

Summary

• 1. Some α,α,α-trichloro- and α,α,α,ω-tetrachloro-alkanes were hydrolyzed by means of hot nitric acid of sp.gr. 1.51-1.52.

• 2. It was shown that the higher trichloro- and tetrachloro-alkanes (11, 13, 15, and 17 carbon atoms) are smoothly hydrolyzed with formation of the corresponding carboxylic and ω-chloro carboxylic acids (having the same number of carbon atoms in their molecules).

• 3. The hydrolysis of aliphatic compounds containing the CHBr-CCl₂Br group by nitric acid of sp.gr. 1.52 proceeds at room temperature with formation of the corresponding α-bromo carboxylic acids in high yield. Neither concentrated sulfuric nor 70 % perchloric acid hydrolyzes compounds of this structure.

• 4. Perchloric acid (70%) hydrolyzes both aliphatic and aromatic compounds containing the CCl₃ or CCl₂=CH group with formation of the corresponding carboxylic acids. Reaction requires comparatively severe conditions (115130°), and it is accompanied by considerable resinification.