Hydrochloric Acid → 1-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

Participants

Reaction Steps

17.8 g (100 mmol) of 2,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxide was dissolved in 100 ml of acetone, and 34 g (300 mmol) of 30% hydrogen peroxide aqueous solution was added slowly for more than 10 minutes. With a cooling to 5° C., 0.49 g (5.0 mol %) of copper (I) chloride was added with keeping the temperature of the reaction mixture in a range of 5° C. to 55° C. After 15 minutes, 0.5 g of 35% hydrochloric acid was added, and the reaction mixture was stirred at room temperature for 2 hours. After 2 hours, 50 ml of 4 mol/L sodium bisulfite aqueous solution, and 100 ml of saturated potassium hydrogen carbonate aqueous solution were added, and an extraction was carried out using 300 mL of ethyl acetate. The organic layer was concentrated by a rotary evaporator to obtain 1-methyloxy-2,2,6,6-tetramethyl-4-hydroxypiperidine.

Provenance & Evidence