Cyclopentadiene → Bicyclo(2.2.1)hept-5-ene-2-carbonyl chloride

Temperature

0 °C

A 1-L, three-neck round-bottom flask equipped with a magnetic stirrer, digital thermometer, glass stopper, an addition funnel with a nitrogen gas purge, and a dry-ice cooling bath was charged with freshly distilled cyclopentadiene (248 g, 3.75 mol), which was cooled to 0° C. The addition funnel was charged with freshly distilled acryloyl chloride (317 g, 3.5 mol), which was added drop wise to the reaction over about three hours while maintaining the reaction temperature between 0-10° C. After the acryloyl chloride addition was complete, the cooling bath was removed and the reaction allowed to warm to room temperature overnight. The reaction mixture was distilled under vacuum, collecting 533 g of the title product distilling at 54-56° C. at a pressure of 300 milliTorr.

1. customdigital thermometer, glass stopper, an addition funnel with a nitrogen gas purge
2. additionwas added drop
3. customwise to the reaction over about three hours
4. temperaturewhile maintaining the reaction temperature between 0-10° C
5. customthe cooling bath was removed
6. temperatureto warm to room temperature overnight
7. distillationThe reaction mixture was distilled under vacuum
8. customcollecting 533 g of the title product
9. distillationdistilling at 54-56° C. at a pressure of 300 milliTorr

ORD record

ord-a721d469489b4148ab97b072f45581ba

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07563558B2