Nitric Acid → HCID 21551516, compound

HRID 268258Notes

Reaction equation

HRID 268258 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH:18]([CH2:20][CH2:21][CH3:22])[CH3:19])([CH2:7][CH2:8][CH3:9])[CH3:6]>O>[CH:18]([O:17][C:12]1[CH:13]=[C:14]([N+:1]([O-:4])=[O:2])[CH:15]=[CH:16][C:11]=1[O:10][CH:5]([CH2:7][CH2:8][CH3:9])[CH3:6])([CH2:20][CH2:21][CH3:22])[CH3:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 21551511HCID 21551511, compound

Product 1

HCID 21551516HCID 21551516, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 300 ml. of conc. HNO3 and 300 ml. of H2O was added dropwise 80 g. (0.32 m.) of o-di(sec-amyloxy)benzene (part A) while maintaining a temperature of 10°C. Stirring was continued for an additional 60 minutes at 10°C, then the solution was poured into 2000 ml. addition was poured into 2000 ml. of ice. The aqueous layer was decanted, and the red oil was dissolved in benzene, dried over anhydrous MgSO4 and concentrated to dryness in vacuo. A chromatographic column 32 inches long with O.D. 3/4 inch, was packed with 20 inches of neutral alumina. The crude product was dissolved in a 250 ml. mixture of 50/50 CHCl3 and CCl4. After the solution was placed on the column, it was washed several times with the same solvent mixture. The first fraction was collected and concentrated to dryness in vacuo to yield 10 g. of amber-colored oil.

Workup

  1. additionTo a mixture of 300 ml
  2. additionthe solution was poured into 2000 ml
  3. additionaddition
  4. additionwas poured into 2000 ml
  5. customThe aqueous layer was decanted
  6. dissolutionthe red oil was dissolved in benzene
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated to dryness in vacuo
  9. dissolutionThe crude product was dissolved in a 250 ml
  10. additionmixture of 50/50 CHCl3 and CCl4
  11. washwas washed several times with the same solvent mixture
  12. customThe first fraction was collected
  13. concentrationconcentrated to dryness in vacuo
  14. customto yield 10 g

Sources & evidence

ORD record
ord-cc38cbea8ed941fc9bda2855c15a1bfe
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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