Hydrochloric Acid → N-[2-(3,4-Dihydroxyphenyl)ethyl]cyclohexanecarboxamide

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Reaction Conditions

Reaction Steps

Dissolve 2.0 g. of the product of Step A carboxylate in 15 ml. of methylene chloride and cool the solution to about -78°C. Add 2.5 g. of boron triiodide and allow the reaction mixture to warm up to about 0°C with vigorous stirring. Stir the reaction mixture at about 0°C overnight, then add about 10 ml. saturated sodium bicarbonate solution. Acidify the mixture with 2N hydrochloric acid and extract with ethyl acetate. Decolorize the extract with aqueous sodium thiosulfate, then wash the extract successively with 2N hydrochloric acid solution, saturated sodium bicarbonate solution, and water. Dry the extract over anhydrous sodium sulfate and evaporate to a residue. Crystallize the residue from a toluene-ethanol mixture to obtain the title product 124°C - 126°C.

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