Diethyl Malonate → HCID 18317327, compound

To a solution of 20% sodium ethoxide in ethanol (6.2 g) were added at room temperature ethanol (150 ml) and diethyl malonate (14.6 g), and then added little by little 4-(2,5-dichlorophenyl)-3-buten-2-one (19.0 g). The mixture was stirred at room temperature for 30 minutes, refluxed for 2 hours and cooled. The solvent was evaporated, and to the residue was added water. The aqueous layer was washed with ethyl acetate and concentrated, and to the residue was added 2M sodium hydroxide (50 ml). The mixture was refluxed for 2 hours and cooled, and to the mixture was added 2.5M sulfuric acid (50 ml) for 15 minutes. The mixture was refluxed for 1.5 hours and cooled, and precipitated crystals were filtered and washed with water and toluene to give 5-(2,5-dichlorophenyl)cyclohexane-1,3-dione (9.9 g) as colorless crystals.

1. temperaturerefluxed for 2 hours
2. temperaturecooled
3. customThe solvent was evaporated
4. additionto the residue was added water
5. washThe aqueous layer was washed with ethyl acetate
6. concentrationconcentrated
7. additionto the residue was added 2M sodium hydroxide (50 ml)
8. temperatureThe mixture was refluxed for 2 hours
9. temperaturecooled
10. additionto the mixture was added 2.5M sulfuric acid (50 ml) for 15 minutes
11. temperatureThe mixture was refluxed for 1.5 hours
12. temperaturecooled
13. customprecipitated crystals
14. filtrationwere filtered
15. washwashed with water and toluene

ORD record

ord-a1dc63ead1a1451ca7ba1b50a2c4642d

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1