1-Bromopropane → Dicyclopentadiene

Participants

Reaction Conditions

Reaction Steps

318.5 grams of the para-cresol icyclopentadiene (PCDP) from above was dissolved in 1100 mL of N-methylpyrrolidinone (NMP) in a 2000 mL 3-neck round bottom flask equipped with mechanical stirrer, addition funnel, condenser, thermometer, nitrogen purge and Therm-O-Watch. To this reaction mixture was added 195.0 g (1.278 moles) of vinylbenzylchloride (60/40 para/meta isomer ratio) and 0.30 g of 2,6-di-tert-butyl-p-cresol (BHT). The reaction mixture was heated to 60° C. and 84.05 g (1.498 moles) of potassium hydroxide in 200 mL of methanol was added dropwise over a 3 hour interval. The reaction was maintained at 60° C. for 16 hrs with stirring under a nitrogen purge. To this reaction mixture was added 49.88 g (0.406 moles) of n-propylbromide, and then 24.43 g (0.435 moles) of potassium hydroxide in 125 mL of methanol added over a 2 hour interval. The reaction was maintained at 60° C. for 4 hours and then allowed to cool to room temperature. The reaction mixture was then transferred to a separatory funnel, and 1.5 Liters of toluene added and then washed once with 4 Liters of water and twice with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under vacuum, yielding a red resinous product; Mn=700, Mw=1600, dispersity of 2.3.

Provenance & Evidence