反応 #64038
ord-7e4825c453c444408c20b24f6f701213
反応方程式
反応条件
後処理
- 1温度the mixture was heated
- 2温度to reflux temperature
- 3workup.ADDITIONwas added over a period of 2 minutes
- 4温度the mixture was heated
- 5温度under reflux for a period of 2 hours
- 6温度the mixture was heated
- 7温度under reflux for a further 41/2 hours
- 8抽出the aqueous mixture was extracted twice with ethyl acetate (100 ml)
- 9温度warmed gently until the evolution of carbon dioxide
- 10抽出The aqueous mixture was extracted with ethyl acetate
- 11乾燥dried over anhydrous sodium sulfate
- 12その他the solvent was removed by evaporation under reduced pressure
- 13その他a rotary evaporator
実験手順
Diethyl malonate (10.1 g; 60 mmole) was added to a solution of sodium metal (1.4 g; 60 mmole) in anhydrous absolute ethanol (50 ml) and the mixture was heated to reflux temperature. A mixture of 1-(2,4,6-trimethylphenyl)but-1-en-3-one (11.4 g; 61 mmole) in anhydrous absolute ethanol (50 ml) 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 (7.3 g; 180 mmole in 100 ml of water) was added and the mixture was heated under reflux for a further 41/2 hours. The solution was poured into water (200 ml) and the aqueous mixture was extracted twice with ethyl acetate (100 ml). The aqueous phase was acidified with concentrated hydrochloric acid and warmed gently until the evolution of carbon dioxide ceased. The aqueous mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The product, 3-hydroxy-5-mesitylcyclohex-2-en-1-one, was obtained as a pale yellow solid (10.9 g; 77.4%), mp 165° C. Proton magnetic resonance spectrum (dimethylsulfoxide; δ in ppm): 2.0-4.1 (14H, m); 5.2 (1H, s); 6.8 (2H, s); 11.2 (1H, br.s).