Structure verification of some chlorinated p-cymenes by high field NMR and IR spectroscopies

Abstract

Seven chlorinated p-cymenes were synthesized by the chlorination of p-cymene and the alkylation of chlorinated toluenes. 2,6-Dichloro-p-cymene was made by the Sandmeyer reaction from 2-amino-6-chloro-p-cymene and 2,3,5-trichloro-p-cymene was synthesized by the chlorination from 3,5-dichloro-p-cymene. The chlorinated compounds were purified by preparative gas chromatography. The coupled 13C NMR spectra of (1) p-cymene, (2) 2-chloro-, (4) 2,3-dichloro-, (8) 2,3,6-trichloro-, and (10) 2,3,5,6-tetrachloro-p-cymenes were recorded by a high field NMR spectrometer and the IR spectra of nine chlorinated p-cymenes were recorded.