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

Temperature

50 °C

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.

1. temperaturewas cooled to rt
2. customwas quenched with saturated NaHCO3 soln
3. extractionand was extracted with CH2Cl2 (3×10 mL)
4. extractionThe combined extract
5. concentrationwas concentrated under reduced pressure
6. dissolutionwas dissolved in MeOH
7. additioncontaining NaOH
8. extractionwas extracted with ethyl acetate (3×10 mL)
9. extractionThe combined extract
10. washwas washed with saturated NaHCO3 solution and brine
11. dry with materialwas dried over anhydrous Na2SO4
12. filtrationwas filtered
13. concentrationwas concentrated under reduced pressure
14. dissolutionThe residue was dissolved in CH2Cl2
15. filtrationwas filtered
16. dry with materialThe DCM solution was dried over anhydrous Na2SO4
17. filtrationwas filtered
18. concentrationwas concentrated under reduced pressure

ORD record

ord-7d71a8bd93e54790bc69379e818fa2a5

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296704B2