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

HRID 1837523Notes

Reaction equation

HRID 1837523 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

At −35° C., 60 g of 4-chromanone are added in small portions to 385 ml of 90% nitric acid. The whole is poured onto ice and then extracted with dichloromethane. The organic phase is washed with a saturated solution of sodium hydrogen carbonate and dried over magnesium sulphate and then the solvent is evaporated off.

Workup

  1. additionThe whole is poured onto ice
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with a saturated solution of sodium hydrogen carbonate
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-21bfbad5cb344a3da004b3f1bf9f0d8f
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Reaction notes

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