반응 #664534

반응 방정식

2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde

m-CPBA

→

2,3-dihydrobenzo[b][1,4]dioxin-6-ol

수율 63.8%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도was cooled to rt
2. 2
   기타was quenched with saturated NaHCO3 soln
3. 3
   추출and was extracted with CH2Cl2 (3×10 mL)
4. 4
   추출The combined extract
5. 5
   농축was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONwas dissolved in MeOH
7. 7
   workup.ADDITIONcontaining NaOH
8. 8
   추출was extracted with ethyl acetate (3×10 mL)
9. 9
   추출The combined extract
10. 10
    세척was washed with saturated NaHCO3 solution and brine
11. 11
    건조was dried over anhydrous Na2SO4
12. 12
    여과was filtered
13. 13
    농축was concentrated under reduced pressure
14. 14
    workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
15. 15
    여과was filtered
16. 16
    건조The DCM solution was dried over anhydrous Na2SO4
17. 17
    여과was filtered
18. 18
    농축was concentrated under reduced pressure

실험 절차

To a stirred solution of 2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde (1 g, 6.09 mmol) in CH2Cl2 (16 mL) was added m-CPBA (4.204 g, 24.36 mmol). The suspension was heated at 50° C. for 2 days, was cooled to rt, was quenched with saturated NaHCO3 soln. and was extracted with CH2Cl2 (3×10 mL). The combined extract was concentrated under reduced pressure, and then was dissolved in MeOH containing NaOH. The solution was stirred at rt for 2 h, was acidified with HCl and was extracted with ethyl acetate (3×10 mL). The combined extract was washed with saturated NaHCO3 solution and brine, was dried over anhydrous Na2SO4, was filtered and was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and was filtered. The DCM solution was dried over anhydrous Na2SO4, was filtered and was concentrated under reduced pressure to give 2,3-dihydrobenzo[b][1,4]dioxin-6-ol (0.591 g, 63%) as a reddish brown oily liquid.

출처