6-nitro-4H-1,3-benzodioxine → HCID 56975056, compound

HRID 358541Notes

Reaction equation

HRID 358541 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[O:8][CH2:9][O:10][CH2:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]>O>[OH:8][C:7]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[CH2:9][O:10][CH2:11][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=[CH:12][C:7]=1[OH:8]

Participants

3

Reactant 1

HCID 2436116-nitro-4H-1,3-benzodioxine

Product 1

HCID 56975056HCID 56975056, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

30 g(0.17 Mol) 6-Nitro-1,3-benzodioxan III are dissolved in 300 ml of certain alcohols. After addition of 15 ml of water 60 ml concentrated sulfuric acid is added dropwise with stirring. The solution is heated under reflux until completely converted to product with the help of a control by thin layer chromatography. After cooling the reaction mixture is mixed with about 200 ml water and the solution is concentrated to about 1/3 of its volume under vacuum. A yellow oil comes down which is extracted with ether. The ether phase is dried by sodium sulfate and the residue is filtered by silica gel with methylene chloride as elution agent. After concentration of the methylene chloride solution light yellow crystals of the corresponding 4-nitrophenol compound precipitate.

Workup

  1. additionis added dropwise
  2. temperatureThe solution is heated
  3. temperatureunder reflux
  4. temperatureAfter cooling the reaction mixture
  5. concentrationthe solution is concentrated to about 1/3 of its volume under vacuum
  6. extractionis extracted with ether
  7. dry with materialThe ether phase is dried by sodium sulfate
  8. filtrationthe residue is filtered by silica gel with methylene chloride as elution agent

Sources & evidence

ORD record
ord-6c8681aacb2242a9b49205087b26c610
Source dataset
uspto-grants-1991_03
Patent number
US04997451

Reaction notes

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