Nitric Acid → 4-Hydroxy-7,8-dimethyl-2H-1-benzopyran-2-one

HRID 1283306Notes

Reaction equation

HRID 1283306 reaction equation
[N+]([O-])(O)=O.C([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[O:13][C:12](=[O:18])[CH:11]=[C:10]2[OH:19])C.[CH:20](Cl)(Cl)Cl>>[CH3:17][C:16]1[C:15]([CH3:20])=[C:14]2[C:9]([C:10]([OH:19])=[CH:11][C:12](=[O:18])[O:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6212ChloroformHCID 547319666-Ethyl-4-hydroxy-7-methyl-2H-1-benzopyran-2-one

Product 1

HCID 547171114-Hydroxy-7,8-dimethyl-2H-1-benzopyran-2-one

Procedure

Fuming nitric acid (16 ml) was added to a stirred suspension of 6-ethyl-4-hydroxy-7-methylcoumarin (m.p. 234°-7° ; 3.17g) in chloroform (250 ml) at room temperature over 1 hour. After standing for a further hour, the solvent was removed in vacuo at room temperature and 6N hydrochloric acid (60 ml) added to the residue. Filtration gave the product, m.p. 170°-2°(d), (C12H11NO5 requires C, 57.83; H, 4.45; N, 5.62. Found: C, 58.07; H, 4.54; N, 5.76).

Workup

  1. waitAfter standing for a further hour
  2. customthe solvent was removed in vacuo at room temperature
  3. addition6N hydrochloric acid (60 ml) added to the residue
  4. filtrationFiltration

Sources & evidence

ORD record
ord-28c516df22e844029e2f973cfdfb891f
Source dataset
uspto-grants-1976_08
Patent number
US03974289

Reaction notes

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