تفاعل #492005

معادلة التفاعل

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

m-CPBA

→

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

المردود 63.8%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas cooled to rt
2. 2
   أخرىwas quenched with saturated NaHCO3 soln
3. 3
   استخلاصand was extracted with CH2Cl2 (3×10 mL)
4. 4
   استخلاصThe combined extract
5. 5
   تركيزwas concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONwas dissolved in MeOH
7. 7
   workup.ADDITIONcontaining NaOH
8. 8
   استخلاصwas extracted with ethyl acetate (3×10 mL)
9. 9
   استخلاصThe combined extract
10. 10
    غسيلwas washed with saturated NaHCO3 solution and brine
11. 11
    تجفيفwas dried over anhydrous Na2SO4
12. 12
    ترشيحwas filtered
13. 13
    تركيزwas concentrated under reduced pressure
14. 14
    workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
15. 15
    ترشيحwas filtered
16. 16
    تجفيفThe DCM solution was dried over anhydrous Na2SO4
17. 17
    ترشيحwas filtered
18. 18
    تركيزwas concentrated under reduced pressure

الإجراء التجريبي

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.

المصدر