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

HRID 1283305Notes

Reaction equation

HRID 1283305 reaction equation
[N+]([O-])(O)=O.C[C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH3:16])[CH:15]=1)[O:12][C:11](=[O:17])[CH:10]=[C:9]2[OH:18].[CH:19](Cl)(Cl)Cl>>[CH3:19][C:15]1[C:14]([CH3:16])=[C:13]2[C:8]([C:9]([OH:18])=[CH:10][C:11](=[O:17])[O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6212ChloroformHCID 547109714-Hydroxy-6,8-dimethyl-2H-1-benzopyran-2-one

Product 1

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

Procedure

Fuming nitric acid (13 ml) was added to a stirred suspension of 6,8-dimethyl-4-hydroxycoumarin (m.p. 253°- 255°; 2.21g) in chloroform (200 ml) at room temperature over 2 hours. After standing for a further 2 hours, the solvent was removed in vacuo at room temperature and 6N hydrochloric acid (50 ml) added to the residue. Filtration and recrystallisation from ethanol gave the product, m.p. 169.5°-170°(d), (C11H9NO5 requires C, 56.18; H, 3.86; N, 5.96. Found; C, 56.22; H, 3.99; N, 5.84).

Workup

  1. customthe solvent was removed in vacuo at room temperature
  2. addition6N hydrochloric acid (50 ml) added to the residue
  3. filtrationFiltration and recrystallisation from ethanol

Sources & evidence

ORD record
ord-691fa3ec5d4348fd8707f4649ed1a07c
Source dataset
uspto-grants-1976_08
Patent number
US03974289

Reaction notes

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