反应详情

Diethyl malonate (21.0 g) was added to a solution of sodium metal (3.02 g) in anhydrous absolute ethanol (55 ml) and the mixture was heated to reflux temperature. 1-(3-Methoxy-2,4,6-trimethylphenyl)but-1-en-3-one (27.3 g) was added over a period of 2 minutes and the mixture was heated under reflux for a period of 2 hours. An aqueous solution of sodium hydroxide (16.0 g in 100 ml of water) was added and the mixture was heated under reflux for a further 41/2 hours. The aqueous mixture was cooled and washed with dichloromethane and the aqueous phase was warmed, acidified with dilute aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure to give 3-hydroxy-5-(3-methoxy-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (20.5 g) as a colourless crystalline solid, mp 165°-166° C.

1. temperaturethe mixture was heated
2. temperatureto reflux temperature
3. temperaturethe mixture was heated
4. temperatureunder reflux for a period of 2 hours
5. temperaturethe mixture was heated
6. temperatureunder reflux for a further 41/2 hours
7. temperatureThe aqueous mixture was cooled
8. washwashed with dichloromethane
9. temperaturethe aqueous phase was warmed
10. extractionextracted with ethyl acetate
11. washThe ethyl acetate phase was washed with water
12. dry with materialdried over anhydrous sodium sulfate
13. customthe solvent evaporated under reduced pressure