Nitric Acid → HCID 86733824, compound

HRID 1283314Notes

Reaction equation

HRID 1283314 reaction equation
[N+]([O-])(O)=[O:2].C(O[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[O:19][C:18](=[O:23])[CH:17]=[C:16]2[OH:24])C1C=CC=CC=1.[OH-:25].[Na+]>C(Cl)(Cl)Cl.C1C=CC=CC=1.O>[OH2:2].[OH:24][C:16]1[C:15]2[C:20](=[CH:21][C:22]([OH:25])=[CH:13][CH:14]=2)[O:19][C:18](=[O:23])[CH:17]=1

Participants

7

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 547049666-(Benzyloxy)-4-hydroxy-2H-1-benzopyran-2-one

Product 1

HCID 86733824HCID 86733824, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Fuming nitric acid (13 ml) was added to a stirred suspension of 6-benzyloxy-4-hydroxycoumarin (m.p. 226°-8°; 3.13g) in chloroform (200 ml) at room temperature over 1.5 hours. After a further 1.5 hours, the solvent was removed in vacuo at room temperature and water (100 ml) added to the residue. Filtration gave an oily solid which was dissolved in benzene, filtered, and the filtrate evaporated to dryness to give a yellow solid, decomp. 170°. The solid was suspended in water (30 ml) and dilute sodium hydroxide solution added till the pH of the solution reached 14. Filtration gave the product, m.p. 262°-4°(d). (C10H10NO6Na requires C, 57.32; H, 3.01; N, 4.18; Na, 6.86. Found: C, 57.44; H, 3.31; N, 4.34; Na, 6.86. Found: C, 57.44; H, 3.31; N, 4.34; Na, 6.67) after washing with water and drying under vacuum.

Workup

  1. customthe solvent was removed in vacuo at room temperature
  2. additionwater (100 ml) added to the residue
  3. filtrationFiltration
  4. customgave an oily solid which
  5. filtrationfiltered
  6. customthe filtrate evaporated to dryness
  7. customto give a yellow solid
  8. custom170°
  9. filtrationFiltration

Sources & evidence

ORD record
ord-bdc3171a51e04710ad86e7a0a30b023a
Source dataset
uspto-grants-1976_08
Patent number
US03974289

Reaction notes

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