Diethyl Malonate → 5-(5-Chloro-2-methoxyphenyl)cyclohexane-1,3-dione

To a solution of 20% sodium ethoxide in ethanol (2.3 g) was added at room temperature diethyl malonate (5.4 g) and then was added little by little 4-(5-chloro-2-methoxyphenyl)-3-buten-2-one (6.8 g), and the reaction 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. To the residue was added 2M sodium hydroxide (18 ml), and the mixture was refluxed for 2 hours and cooled. To the mixture was added 2.5M sulfuric acid (18 ml) for 15 minutes, and the mixture was refluxed for 15 minutes, cooled and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(5-chloro-2-methoxyphenyl)cyclohexane-1,3-dione (7.3 g) as amorphous.

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 (18 ml)
8. temperaturethe mixture was refluxed for 2 hours
9. temperaturecooled
10. additionTo the mixture was added 2.5M sulfuric acid (18 ml) for 15 minutes
11. temperaturethe mixture was refluxed for 15 minutes
12. temperaturecooled
13. extractionextracted with ethyl acetate
14. washThe organic layer was washed with water and saturated brine
15. dry with materialdried with magnesium sulfate
16. customUnder reduced pressure, the solvent was evaporated

ORD record

ord-3e99606bc58c448ab61e54d7e0e90cd2

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350749B1