1,3-Butadiene → Spiro[5.5]undeca-1,4,8-trien-3-one, 2,4-bis(1,1-dimethylethyl)-

Participants

Reaction Conditions

Reaction Steps

A 300 mL Parr autoclave was charged with a solution of 10.52 g (40 mmols) of N,N-dimethyl-4-aminomethyl-2,6-di-t-butylphenol in 90 g of toluene, sealed and evacuated by a water aspirator, and then charged with 4.38 g (80 mmols) of 1,3-butadiene. The reaction mixture was heated to approximately 205° C. for 10 hours. A maximum pressure of 120 psig was obtained. After cooling, the reaction mixture was poured into a 500 mL separatory funnel, washed with approximately 2N HCl (1×50 mLs), water (1×50 mLs), and brine (1×50 mLs), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 10.21 g (94% yield) of 2,4-di-t-butylspiro[5.5]undeca-1,4,8-trien-3-one as a brown solid. The brown solid was recrystallized from 80% ethanol to give the product as colorless crystals.

Provenance & Evidence