Epichlorohydrin → (7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

HRID 970670Notes

Reaction equation

HRID 970670 reaction equation
C(=O)([O-])O.[Na+].[N+:6]([C:9]1[CH:10]=[C:11]([OH:16])[C:12](=[CH:14][CH:15]=1)[OH:13])([O-:8])=[O:7].[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl>CN(C=O)C.O>[N+:6]([C:9]1[CH:15]=[CH:14][C:12]2[O:13][CH2:17][CH:19]([CH2:20][OH:21])[O:16][C:11]=2[CH:10]=1)([O-:8])=[O:7]

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 516892Sodium BicarbonateHCID 35051094-Nitrocatechol

Product 1

HCID 12736685(7-Nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanolYield 39.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

3.0 g of sodium hydrogen carbonate was suspended in 90 mL DMF. At 0° C. a solution of 5.15 g of 4-nitrocatechol was added dropwise over 15 min. Subsequently, 3.9 g of epichlorohydrin in 10 mL DMF were added over 15 min. Stirring was continued at room temperature, then at 80° C. overnight. The mixture was diluted with water and extracted three times with ethyl acetate, dried (anhyd. Na2SO4), filtered and concentrated under vacuum to give a yellow oil. The oil was purified by column chromatography on silica gel using EtOAc-hexanes (0-100% gradient) to give the product (2.8 g) as a yellow solid.

Workup

  1. customwas continued at room temperature
  2. customat 80° C.
  3. customovernight
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried (anhyd. Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give a yellow oil
  9. customThe oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8251ffdd4442443fb0988d13fadad954
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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