تفاعل #168980

معادلة التفاعل

NaHCO3

2,3-dihydro-benzo[1,4]dioxin-6-carboxaldehyde

mCPBA

→

2,3-dihydro-benzo[1,4]dioxin-6-ol

المردود 96.7%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with CH2Cl2
2. 2
   تركيزThe combined organics were concentrated in vacuo
3. 3
   workup.ADDITION200 ml 4M NaOH was added
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   غسيلThe combined organics were washed with saturated NaHCO3
6. 6
   غسيلwashed with brine
7. 7
   تركيزconcentrated in vacuo
8. 8
   ترشيحThe solution was filtered
9. 9
   أخرىto remove the precipitate
10. 10
    أخرىseparated
11. 11
    تجفيفdried over MgSO4
12. 12
    ترشيحfiltered
13. 13
    تركيزconcentrated in vacuo

الإجراء التجريبي

To a solution of 2,3-dihydro-benzo[1,4]dioxin-6-carboxaldehyde (30.0 g, 183 mmol) in 500 ml CH2Cl2 was added mCPBA (37.85 g, 219 mmol). The suspension was heated to 50° C. After 16 h saturated NaHCO3 was added and the mixture was extracted with CH2Cl2. The combined organics were concentrated in vacuo and taken up in MeOH and 200 ml 4M NaOH was added. After 2 h the mixture was acidified with 4M HCl and extracted with ethyl acetate. The combined organics were washed with saturated NaHCO3, washed with brine, concentrated in vacuo, and taken up in CH2Cl2. The solution was filtered to remove the precipitate. The resulting solution was stirred with saturated NaHCO3 for 1 h, separated, dried over MgSO4, filtered and concentrated in vacuo to give 2,3-dihydro-benzo[1,4]dioxin-6-ol (26.92 g, 94%).

المصدر