Potassium Hydroxide → HCID 10569169, compound

Participants

Reaction Steps

To a solution of 85% KOH (0.5 g, 7.57 mmol) in 50 mL of methanol was added compound 3 (2.50 g, 5.97 mmol). After overnight stirring, thin layer chromatography indicated very little reaction progress so the reaction mixture was refluxed under argon for several minutes. Chromatographic analysis still indicated little reaction progress so the reaction mixture was cooled. Additional KOH (0.53 g) was added and reflux was continued another 15 minutes. After this period of time, the starting material was completely consumed. The reaction mixture was concentrated, and the residue was partitioned between methylene chloride and water. The layers were separated, and the aqueous layer was further extracted with methylene chloride. The organic extracts were combined, washed with brine, and dried (MgSO4). The organic extract was concentrated to provide an oil which was dissolved in isopropanol and filtered through MgSO4. To the filtrate was added maleic acid (0.725 g), and the resulting mixture was concentrated in vacuo to provide an oil which was partitioned between 3N NaOH and methylene chloride. The layers were separated and the aqueous layer was extracted with dichloromethane. The organic extracts were combined, washed with brine, and dried (MgSO4). The organic extract was concentrated, and the resulting oil was purified on TLC mesh silica (97:3 methylene chloride:methanol). The purified material was dissolved in ethyl ether and added to ethereal HCl. The resulting precipitate was collected by suction filtration and washed with ether. The sample was dried to provide 1.72 g (70%) of benzyl alcohol dihydrochloride 4, mp 201° C. (dec). The 1H NMR supported the desired structure.

Provenance & Evidence