Acetic Acid → Neopinone

참여 물질

반응 조건

반응 단계

A solution of thebaine (1.00 g., 3.22 mmol) in methanol (40 ml.) was added to a stirred suspension of mercuric acetate (1.54 g., 4.82 mmol, 150 mol%) in methanol (30 ml.) at reflux for 50 min. under N2. After reflux, the mixture was filtered and the solvent evaporated in vacuo to give 2.67 g. of residue. This residue was taken up in 100 ml. of 3N acetic acid (17 ml. glacial HOAc diluted to 100 ml. H2O) and stirred at room temperature under N2 for 100 min. at which time 70 ml. of sat. aq. KBr was added to ppt. HgBr2. The precipitated mercury salts were filtered off through filter-aid after stirring for about 1 hour. The filtrate was cooled to 0° C. and 50 ml. of chloroform was added. The aqueous phase was basified to pH 12 with concentrated aq. NaOH. The chloroform layer was separated and the aqueous layer extracted with several portions of chloroform. All of the chloroform extracts were combined, washed with water, dried over Na2SO4, filtered and evaporated in vacuo to give crystalline neopinone; 0.995 g. (100%).

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