CN([CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[C:7]([CH3:13])[CH:6]=1)C.CI.[CH2:16]=[CH:17][CH:18]=[CH2:19]>C(OCC)(=O)C>[CH3:13][C:7]1[C:8](=[O:12])[C:9]([CH3:11])=[CH:10][C:5]2([CH2:19][CH2:18][CH:17]=[CH:16][CH2:4]2)[CH:6]=1To a 250 mL glass reaction vessel containing an ethyl acetate (120 mLs) solution of N,N-dimethyl,2,6-dimethyl-4-aminomethylphenol (3.58 g; 20 mmols), there was added methyl iodide (20 mmols) to give a colorless slurry. The reaction vessel was sealed and 1,3-butadiene (100 mmols) was introduced into the system. The reaction mixture was heated to 120° C. and the pressure was increased from atmospheric up to 70 psig. The reaction mixture was maintained at these conditions for approximately 16 hours. The reaction vessel was then cooled to room temperature. After cooling, the reaction mixture was filtered to remove ammonium iodide salt by-product. The filtrate was concentrated to afford a viscous oil which was crystallized from ethanol to give 3.3 g of 2,4-dimethylspiro[5.5]undeca-1,4,8-trien-3-one (84% yield by vapor phase chromatography).
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