Abstract
By the reaction of N-acetyl-p-toluidine and chloral in conc. sulfuric acid, with the addition of phosphoryl chloride, at 25-35°, an acid ArCHClCOOH and a small amount of ArCHClCCl3 were obtained. The latter does not undergo decomposition under these conditions so that the formation of the acid must be due to the decomposition of chloral to an acid and its bonding with the aromatic ring. When the same reaction is carried out at 70°, there is formation of ArCHO and Ar2CHCOOH as by-products which are formed secondarily from the corresponding hydroxy acid formed from ArCHClCOOH. Since these aldehyde and acid are not formed at a low temperature, the acid formed by the decomposition of chloral must be +CHClCOOH and not +CH(OH)COOH.It may be assumed that chloral undergoes the same decomposition in conc. sulfuric acid as in the presence of alkali, even in a slight degree, to form -CCl3 and +CHO, which makes it possible to understand the formation of chloralide by the foregoing mechanism. In this reaction, -CCl3 combines with +CHClCOOH to form CCl3CHClCOOH, which changes to the corresponding α-hydroxy acid, and finally combines with chloral to form the chloralide. At lower temperatures, chloralide is hardly formed and the fact that it is formed in a large amount under conditions that allows the formation of ArCHO and Ar2CHCOOH secondarily from ArCHClCOOH supports this assumption.
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