Codeine has been converted into isocodeine in overall yields of 65–70%. Codeine toluene-p-sulphonate reacted in benzene with hexadecyltrimethylammonium acetate to give isocodeine acetate, which was hydrolysed to isocodeine. Reinecke's salt was used to remove the hexadecyltrimethylammonium cation from the reaction mixture. The codeine content of the purified isocodeine was assayed by radiodilution techniques.
G. W. Kirby and S. R. Massey, J. Chem. Soc. C, 1971, 3047 DOI: 10.1039/J39710003047
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