反应 #64051

反应方程式

2-butyryl-3-hydroxy-5-mesitylcyclohex-2-en-1-one

dichloromethyl methyl ether

→

2-butyryl-3-hydroxy-5-(3-formyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one

收率 26.7%

溶剂

dichloroethane

dichloroethane

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise over a 25 minute period
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGthe mixture was stirred for 5 minutes at 0° C., for 30 minutes at room temperature and for 2 hours
4. 4
   温度under reflux
5. 5
   其他The cooled reaction mixture
6. 6
   workup.ADDITIONwas poured into a separatory funnel
7. 7
   workup.ADDITIONcontaining
8. 8
   其他crushed ice
9. 9
   workup.STIRRINGwas shaken thoroughly
10. 10
    其他The organic layer was separated
11. 11
    萃取the aqueous solution was extracted with methylene chloride
12. 12
    洗涤The combined organic solution was washed with water
13. 13
    干燥dried over anhydrous sodium sulfate
14. 14
    其他evaporated to dryness
15. 15
    其他to give a crude brown oil (0.70 g)
16. 16
    其他Purification by column chromatography over silica gel (eluant dichloromethane)

实验过程

To a solution of 2-butyryl-3-hydroxy-5-mesitylcyclohex-2-en-1-one (1.20 g) in dichloroethane (20 ml) at 0° C. was added titanium tetrachloride (300 g) over a period of 3 minutes. While the solution was stirred and cooled dichloromethyl methyl ether (0.46 g) in dichloroethane(20 ml) was added dropwise over a 25 minute period. After the addition was complete, the mixture was stirred for 5 minutes at 0° C., for 30 minutes at room temperature and for 2 hours under reflux. The cooled reaction mixture was poured into a separatory funnel containing crushed ice and was shaken thoroughly. The organic layer was separated, and the aqueous solution was extracted with methylene chloride. The combined organic solution was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give a crude brown oil (0.70 g). Purification by column chromatography over silica gel (eluant dichloromethane) gave 2-butyryl-3-hydroxy-5-(3-formyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.35 g) as a pale yellow oil. Proton nuclear magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.0 (3H, t); 1.68 (2H, m); 2.43 (3H, s); 2.48 (3H, s); 2.61 (3H, s); 2.65-4.20 (7H, m); 6.94 (1H, s); 10.54 (1H, s); 18.33 (1H, s).

来源