Nitric Acid → 6-nitro-3,4-dihydro-2H-1-benzopyran-4-one

HRID 862425Notes

Reaction equation

HRID 862425 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[O:1][CH2:2][CH2:3][C:4]2=[O:11])([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 68110Chromanone

Product 1

HCID 52288316-nitro-3,4-dihydro-2H-1-benzopyran-4-one

Procedure

Fuming nitric acid (200 ml) was cooled to from -30° to -35° C. and 4-chromanone (29.0 g) was added with stirring over 30 minutes. The mixture was further stirred for 30 minutes at the intact temperature and successively poured into ice water. The resulting mixture was extracted with ethyl acetate (2,500 ml). The organic layer was dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain the crude product as a yellow solid. The crude product was washed with a solvent mixture, n-hexane:ethyl acetate=1:1, to obtain 6-nitro-4-chromanone (27.0 g).

Workup

  1. additionwas added
  2. stirringThe mixture was further stirred for 30 minutes at the intact temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate (2,500 ml)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain the crude product as a yellow solid
  7. washThe crude product was washed with a solvent mixture, n-hexane

Sources & evidence

ORD record
ord-2232ac656e184c4ea27da9d00d462c44
Source dataset
uspto-grants-1998_02
Patent number
US05719145

Reaction notes

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