Zincke; and his researches have led to the discovery of many chlorinated oxidation products which admit of decomposition into cyclic compounds containing fewer carbon atoms than characterize the benzene ring, and in turn yielding openchain or aliphatic compounds.
This latter compound may be chlorinated to perchloracetoacrylic chloride (9), from which the corresponding acid (to) is obtained by treatment with water; alkalis hydrolyse the acid to chloroform and dichlormaleic acid (I I).
When thus chlorinated phenol (I) yields trichlor-o-diketo-R-hexene (2), which may be hydrolysed to an acid (3), which, in turn, suffers rearrangement to trichlor-R-pentene-oxycarboxylic acid (4).
This is shown in the case of the chloracetic acids: According to van 't Hoff the substitution of chlorine atoms into a methyl group occasions the following increments: The introduction of chlorine, however, may involve a fall in the boiling-point, as is recorded by Henry in the case of the chlorinated acetonitriles: NC CH 3.
When treated with hydrochloric acid and potassium chlorate, no chlorinated quinones are obtained (M.
In the preparation of chloroform by the action of bleaching powder on ethyl alcohol it is probable that the alcohol is ..rst oxidized to acetaldehyde, which is subsequently chlorinated and then decomposed.
A number of organic chlorinated products are also produced on a large scale.
Kulisch, Monats., 1894, 15, p. 276); by the action of phosphorus pentachloride on hydrocarbostyril (the inner anhydride of ortho-aminohydrocinnamic acid), the chlorinated compound first formed being then reduced by hydriodic acid (A.
Gabriel, Ber., 1886, 9, 1655, 2355): '/C It /CH = C(OH) CH= C Cl /CH=CH C 6 114 I or C 6 H4< - C 6 H4< --> C6H4< CO-NH C(OH): N CH= It is also formed from isobenzalphthalide by the action of ammonia, followedby phosphorus oxychloride and reduction of the chlorinated product (S.