Hydrochloric Acid → HCID 69530634, compound

1.5 g of sodium borohydride was added to a mixture of 20.5 g of 2-propionyl-1,8-difluorofluorene (K-2) and 100 ml of methanol at a temperature of −10° C., and the temperature was gradually raised, and then held at 0° C. for two hours to allow the reaction to proceed. Following completion of the reaction, 30 ml of 1N dilute hydrochloric acid was added to the cooled reaction mixture, and the methanol was then removed by evaporation under reduced pressure. The residue was then extracted into 100 ml of toluene. The organic layer was washed with 100 ml of water. Following drying, 1.0 g of p-toluenesulfonic acid monohydrate was added, and the mixture was refluxed under heat for one hour. The reaction mixture was then cooled to room temperature, 7 ml of a 1N aqueous solution of sodium bicarbonate was added to neutralize the mixture, and the mixture was then washed with 100 ml of water. Following drying, the solvent was removed by evaporation to yield 19.3 g (crude product) of 2-(propen-1-yl)-1,8-difluorofluorene (K-3). This product was used without purification in the subsequent reaction.

1. temperaturethe temperature was gradually raised
2. customthe reaction
3. additionwas added to the cooled reaction mixture
4. customthe methanol was then removed by evaporation under reduced pressure
5. extractionThe residue was then extracted into 100 ml of toluene
6. washThe organic layer was washed with 100 ml of water
7. customFollowing drying
8. addition1.0 g of p-toluenesulfonic acid monohydrate was added
9. temperaturethe mixture was refluxed
10. temperatureunder heat for one hour
11. addition7 ml of a 1N aqueous solution of sodium bicarbonate was added
12. washthe mixture was then washed with 100 ml of water
13. customFollowing drying
14. customthe solvent was removed by evaporation

ORD record

ord-7d3959fe2ae74a2096b563c727650b1b

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067179B1