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UBC Theses and Dissertations

Some intermediates for the synthesis of [beta](3-methoxy-4-hydroxy-phenyl)-[beta]-hydroxy-ethylamine, Part II Attree, Richard Willoughby Alec

Abstract

The synthesis of β-(3-methoxy-4-hydroxy phenyl-)-β-hydroxy ethylamine was attempted, as the initial step in the investigation of its pharmacological properties. Attempted reduction of 3-methoxy-4-hydroxy-ω-nitrostyrene gave no isolated products. Bromination of the side chain of the nitrostyrene, followed by treatment with potassium acetate and potassium hydroxide in methanol gave an amorphous material and not the expected β-(3-methoxy-4-hydroxy phenyl-)-β,β-dimethoxy-nitroethane. Vanillin was then converted into benzoyl vanillyl chloride which on treatment with diazomethane, gave the substituted ω-diazoacetophenone which in turn was converted through the ω-chloro derivative to the ω-iodoacetophenone. This was condensed with hexamethylene tetramine. Further work on the problem is under way.

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