Nitric Acid → HCID 602086, compound

HRID 2291106Notes

Reaction equation

HRID 2291106 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1)=[O:3].[N+:12]([O-])([OH:14])=[O:13]>O>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:5]=1[N+:12]([O-:14])=[O:13])=[O:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 114603-Methoxyacetophenone

Product 1

HCID 602086HCID 602086, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

50.0 g of 3-methoxyacetophenone was slowly added drop-by-drop to 250 ml of 70% nitric acid at room temperature. After 17 hours, the resulting solution was warmed to 40° C. and held for one hour. The mixture was cooled, diluted with three times its volume of water and extracted with ethyl acetate. The extract was washed with water, then brine, dried (NaSO4), and the solvent was evaporated. The residue was dissolved in ethyl acetate. Hexane was added and the mixture was set in dry ice. The solid material that formed was separated and dried under reduced pressure, to give 3-methoxy-2-nitroacetophenone (5A), as a cream colored solid, m.p.: 125°-127° C.

Workup

  1. waitheld for one hour
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialbrine, dried (NaSO4)
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. additionHexane was added
  9. customThe solid material that formed
  10. customwas separated
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-9095775b650c4f45b1c400993f09c7df
Source dataset
uspto-grants-1986_10
Patent number
US04620000

Reaction notes

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