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UBC Theses and Dissertations

The synthesis of some secondary amyl and hexyl homologues of dinitro ortho and paracresols Moffatt, John Gilbert


Eight new dinitro-sec.-amyl and hexylphenols of unequivocal structure were synthesized and characterized by their piperidine, morpholine and cyclohexylamine salts. The synthetic route followed involves the Fries rearrangement, of phenyl acetate and phenyl propionate to give the easily separated isomers o- and p-hydroxyacetophenone and o- and p-hydrcocypropiophenone. These compounds were then methylated to give the corresponding methoxyacetophenones and methoxypropiophenones. The methylated aryl-alkyl ketones were condensed through a Grignard reaction with various alkyl bromides to give tertiary alcohols which were dehydrated by the Dean and Stark method to the corresponding olefins and then hydrogenated to alkylanisoles. Demethylation was effected through the use of pyridine hydrobrondde for the p-alkylphenols, or 47% hydriodic acid and phenol for the o-alkylphenols. The alkyl phenols were then nitrated with fuming nitric acid in glacial acetic acid at -15⁰C., and the resulting dinitro-alkylphenols characterized as amine salts. The phenols prepared were: 3-(o- and p-hydroxyphenyl)-pentane, 2-(o- and p-hydroxyphenyl)-hexane, 2-(o- and p-hydroxyphenyl)-3-methylpentane, 2-(o- and p-hydroxyphenyl)-4-methylpentane. Of these, only 2-(p-methoxyphenyl)-3-mathylpentane has been reported prepared by an unequivocal synthesis. All other phenols, their intermediates and derivatives, and their dinitro derivatives, are previously unreported except in odd cases through questionable condensation methods.

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