Methyl iodide → 2,4-Dimethylspiro[5.5]undeca-1,4,8-trien-3-one

Participants

Reaction Conditions

Reaction Steps

To 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).

Provenance & Evidence