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 (7.16 g; 40 mmols), there was added methyl iodide (40 mmols) to give a colorless slurry. The vessel was sealed and 1,3-butadiene (200 mmols) was introduced into the vessel. The reaction mixture was heated to 130° C. and the pressure was increased from atmospheric to 70 psig. The reaction mixture was maintained at these conditions for approximately 5 hours. The reaction vessel was 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 purified by column chromatography (ethyl acetate/silica gel) to give 6.02 g of 2,4-dimethylspiro[5.5]undeca-1,4,8-trien-3-one (76% yield by vapor phase chromatography).
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