Acetone → 1-Cyclopropyl-butane-1,3-dione

Boron trifluoride gas is introduced for one hour at 40° C. into a mixture of 191 g of cyclopropanecarboxylic acid and 45 g of acetone. There is formed a black oily product, which is diluted with 800 ml of ether. The ether phase is then washed 4 times with 300 ml of water each time, and, with ice cooling, 30% sodium hydroxide solution is finally added until the pH value is ~9. The ether layer is separated, and the aqueous phase is extracted three times with 300 ml of ether each time. The ether phases are collected, dried over sodium sulfate, purified with active charcoal, filtered, and concentrated by evaporation. The oil which remains is purified by chromatography through a silica gel column with ether/hexane (1:3) as the eluant. The yield after removal of the solvent by evaporation is 22 g of the title compound as light-coloured oil; refractive index nD24 : 1.488.

1. customThere is formed a black oily product, which
2. washThe ether phase is then washed 4 times with 300 ml of water each time
3. additionwith ice cooling, 30% sodium hydroxide solution is finally added until the pH value
4. customThe ether layer is separated
5. extractionthe aqueous phase is extracted three times with 300 ml of ether each time
6. customThe ether phases are collected
7. dry with materialdried over sodium sulfate
8. custompurified with active charcoal
9. filtrationfiltered
10. concentrationconcentrated by evaporation
11. customThe oil which remains is purified by chromatography through a silica gel column with ether/hexane (1:3) as the eluant
12. customThe yield
13. customafter removal of the solvent
14. customby evaporation

ORD record

ord-f4dbe6f88e124ddf9ce9aaeb57360744

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04600428