Nitric Acid → HCID 20224554, compound

HRID 1381969Notes

Reaction equation

HRID 1381969 reaction equation
[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15].[N+:22]([O-])([OH:24])=[O:23]>>[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]([N+:22]([O-:24])=[O:23])[C:13]=1[CH:14]=[O:15]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 20224539HCID 20224539, compound

Product 1

HCID 20224554HCID 20224554, compound

Conditions

Temperature
15 °C

Procedure

2-Hydroxy-3-methoxybenzaldehyde benzenesulfonate (200 g, 0.685 mole) was added to 90% nitric acid (400 mL) with the temperature maintained at 0° ±2° over a period of one-half to one hour. The reaction mixture was stirred an additional 0.5 hour and poured over ice (2.5 L) with stirring. After standing several hours, the solid was collected by filtration and washed with water (500 mL). The solid was then suspended in acetone (1.25 L) and the mixture was heated to reflux for 0.5 hour, concentrated to 500 mL and cooled to 15° C. The resultant solid was collected by filtration and washed with cold acetone (125 mL) to provide the title compound, 138.5 g (60%), mp 151°-155° C.

Workup

  1. temperaturemaintained at 0° ±2° over a period of one-half to one hour
  2. stirringwith stirring
  3. waitAfter standing several hours
  4. filtrationthe solid was collected by filtration
  5. washwashed with water (500 mL)
  6. temperaturethe mixture was heated
  7. temperatureto reflux for 0.5 hour
  8. concentrationconcentrated to 500 mL
  9. filtrationThe resultant solid was collected by filtration
  10. washwashed with cold acetone (125 mL)

Sources & evidence

ORD record
ord-0844a1a613544788b59d85a3e76b65d1
Source dataset
uspto-grants-1989_02
Patent number
US04804756

Reaction notes

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