반응 #64051

반응 방정식

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

수율 26.7%

용매

dichloroethane

dichloroethane

반응 조건

후처리

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
   온도under reflux
5. 5
   기타The cooled reaction mixture
6. 6
   workup.ADDITIONwas poured into a separatory funnel
7. 7
   workup.ADDITIONcontaining
8. 8
   기타crushed ice
9. 9
   workup.STIRRINGwas shaken thoroughly
10. 10
    기타The organic layer was separated
11. 11
    추출the aqueous solution was extracted with methylene chloride
12. 12
    세척The combined organic solution was washed with water
13. 13
    건조dried over anhydrous sodium sulfate
14. 14
    기타evaporated to dryness
15. 15
    기타to give a crude brown oil (0.70 g)
16. 16
    기타Purification by column chromatography over silica gel (eluant dichloromethane)

실험 절차

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).

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