m-Chloroperbenzoic acid → 2,3-Dihydro-1,4-benzodioxin-6-ol

Temperatur

50 °C

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%).

1. extractionthe mixture was extracted with CH2Cl2
2. concentrationThe combined organics were concentrated in vacuo
3. addition200 ml 4M NaOH was added
4. extractionextracted with ethyl acetate
5. washThe combined organics were washed with saturated NaHCO3
6. washwashed with brine
7. concentrationconcentrated in vacuo
8. filtrationThe solution was filtered
9. customto remove the precipitate
10. customseparated
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo

ORD-Eintrag

ord-10e17ce04909466bbe943ced7fe55787

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846705B2