Reaktion #66659

Reaktionsgleichung

NaHCO3

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

mCPBA

→

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

Ausbeute 96.7%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with CH2Cl2 The combined
2. 2
   Einengenorganics were concentrated in vacuo
3. 3
   workup.ADDITION200 ml 4M NaOH was added
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe combined organics were washed with saturated NaHCO3
6. 6
   Waschenwashed with brine
7. 7
   Einengenconcentrated in vacuo
8. 8
   FiltrationThe solution was filtered
9. 9
   Sonstigeto remove the precipitate
10. 10
    Sonstigeseparated
11. 11
    Trocknendried over MgSO4
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated in vacuo

Vorschrift

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%).

Quelle