Abstract
Attempts have been made to determine the structures of chloromethylated products obtained by chloromethylation of alkyl-or alkoxybenzenes having chloro or nitro group in 3-position, such as 3-nitroanisole (1), 3-chloroanisole (2), 3-chlorophenetole (3), 3-chlorotoluene (4), 3-chloroethylbenzene (5), 3-nitrotoluene (6), and 3-nitroethylbenzene (7).(1)-(5) were obtained by using glacial acetic acid as a solvent and anhydrous zinc chloride as a catalyst and by chloromethylation with paraformaldehyde and dry hydrogen chloride gas.(6) and (7) were obtained by chloromethylation with dichloromethyl ether and chlorosulfonic acid.The position of entrance of chloromethyl group were examined and it was found that (1), (2), and (4)(7) were composed of a mixture of 4-substituent and 6-substituent.(3) gave 4-substituent only as in the case of 3-nitrophenetole and the presence of 6-substituent could not be confirmed.
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