Nitric Acid → HCID 14091388, compound

HRID 268281Notes

Reaction equation

HRID 268281 reaction equation
[N+:1]([O-:4])(O)=[O:2].O.[CH2:6]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:7][CH:8]([CH3:10])[CH3:9].C(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[CH2:19]([O:18][C:13]1[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=[CH:17][C:12]=1[O:11][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:20][CH:21]([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 6212ChloroformHCID 10955985HCID 10955985, compound

Product 1

HCID 14091388HCID 14091388, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 300 ml. of conc. HNO3 and 300 ml. of H2O was added dropwise 90 g. (0.36 m.) of o-diisoamyloxybenzene while maintaining a temperature of 19°-21°C. Stirring was continued for an additional 60 minutes at 19°-21°C, then the solution was poured into 3 liters of ice. The crude product was collected by filtration, washed with cold H2O and airdried to give 90 g. It was recrystallized from 300 ml. of MeOH to give 25.5 g. A chromatographic column, 32 inches long with O.D. 3/4 inch, was packed with 20 inches of neutral alumina. The 25 g. of crude product was dissolved in a 250 ml. mixture of 50/50 CHCl3 and CCl4. After the mixture was placed on the column, it was washed several times with the same solvent mixture. The first fraction, very light yellow in color, was collected and concentrated to dryness in vacuo to yield 15 g. m.p. 44°-47°C.

Workup

  1. additionTo a mixture of 300 ml
  2. filtrationThe crude product was collected by filtration
  3. washwashed with cold H2O
  4. customto give 90 g
  5. customIt was recrystallized from 300 ml
  6. customof MeOH to give 25.5 g
  7. dissolutionof crude product was dissolved in a 250 ml
  8. washwas washed several times with the same solvent mixture
  9. customThe first fraction, very light yellow in color, was collected
  10. concentrationconcentrated to dryness in vacuo
  11. customto yield 15 g

Sources & evidence

ORD record
ord-e2dc6bb1c5b9445c8b62ec380c3ca9c9
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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