5-(4-methoxyphenyl)cyclohexane-1,3-dione → HCID 18317344, compound

A mixture of 5-(4-methoxyphenyl)cyclohexane-1,3-dione (0.95 g), dimethyl-1,2-propadien-1-yl sulfonium bromide (1.5 g), sodium ethoxide (0.31 g) and ethanol (10 ml) was refluxed for 5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in toluene (20 ml), and to the solution was added p-toluenesulfonic acid(0.85 g). The mixture was stirred at room temperature for 1 hour. To the mixture was added ethyl acetate, and the mixture was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 6-(4-methoxyphenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.14 g).

1. temperaturewas refluxed for 5 hours
2. customUnder reduced pressure, the solvent was evaporated
3. dissolutionthe residue was dissolved in ethyl acetate
4. washThe solution was washed with water and saturated brine
5. dry with materialdried with magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in toluene (20 ml)
8. additionto the solution was added p-toluenesulfonic acid(0.85 g)
9. additionTo the mixture was added ethyl acetate
10. washthe mixture was washed with sodium hydrogen carbonate solution, water and saturated brine
11. dry with materialdried with magnesium sulfate
12. concentrationconcentrated under reduced pressure
13. customThe residue was purified with silica gel column chromatography (EtOAc/hexane)

ORD record

ord-a16b2ba41dde4b51884dc275e0aea271

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1