Hydrochloric Acid → 2,2,6,6-Tetramethyl-4-piperidone

Participants

Reaction Steps

In a 500 mL erlenmeyer flask, 25 gm (0.182 moles) of phorone (Aldrich Chemical Company) and 250 mL of ammonium hydroxide are stirred in a water bath at 50° C. for 14 hours. Upon cooling in an ice bath, the reaction is acidified with conc. HCl and extracted (four times) with ether. The remaining water solution is first made basic with ammonium hydroxide, then saturated with NaCl and finally, extracted with ether. The ether solution is dried over anhydrous MgSO4 and evaporated to dryness, giving a pale yellow solid (I), (17 gm, 60%). A small portion of this material is recrystallized from cyclohexane, mp 34°-36° C. (lit. ref. 1) mp 35.5°-36° C.). The NMR and i.r. (1750 cm-1) confirm the presence of 4-oxo-2,2,6,6-tetramethylpiperidine.

Provenance & Evidence