Phosphorus oxide (P4O10) → 6-nitro-3,4-dihydro-2H-1-benzopyran-4-one

HRID 493139Notes

Reaction equation

HRID 493139 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][C:11]2=[O:13])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 3515353-(4-Nitrophenoxy)propionic acid

Product 1

HCID 52288316-nitro-3,4-dihydro-2H-1-benzopyran-4-oneYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(4-nitrophenoxy)propanoic acid (6.5 g, 30 mmol), concentrated sulfuric acid (30 mL) and phosphorus pentoxide (5.2 g, 37 mmol) is stirred at 60° C. for 3 hours, poured onto ice, stirred for 15 minutes and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a beige solid, 5.5 g (94% yield) mp 171-173° C., identified by NMR and mass spectral analyses.

Workup

  1. additionpoured onto ice
  2. stirringstirred for 15 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f12492a915ed4c0a8c8bc209850d7b41
Source dataset
uspto-grants-2009_05
Patent number
US07534801B2

Reaction notes

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