Acetic Acid → HCID 20042539, compound

HRID 1762188Notes

Reaction equation

HRID 1762188 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=C(C)[C:3]=1[CH2:4][O:5][C:6]1[C:7]([N+:12]([O-:14])=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1.C(OC(=O)C)(=[O:22])C.S(=O)(=O)(O)O.[C:32]([OH:35])(=O)[CH3:33]>[O-2].[O-2].[O-2].[Cr+6]>[CH:1]([C:2]1[CH:18]=[CH:17][CH:16]=[C:33]([CH:32]=[O:35])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([N+:12]([O-:14])=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 14368407HCID 14368407, compound

Product 1

HCID 20042539HCID 20042539, compound

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Procedure

To a suspension of 3-(2,6-dimethylbenzyloxy)-2-nitropyridine (2.6 g) in a mixture of acetic acid (26 ml), acetic anhydride (39 ml) and sulfuric acid (5 ml) was added chromium trioxide (2.5 g) portionwise during a period of 20 minutss at 10° C. After being stirred for 2 hours at the same temperature the reaction mixture was poured into ice-water and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl alcohol and the solution was made strongly basic to litmus with an aqueous solution of 24% sodium hydroxide with ice-cooling. After being stirred for 2.5 hours at an ambient temperature, the mixture was diluted with ice water. The resulting precipitates were filtrated off and dried to give a mixture (1.29 g) of 3-(2,6-diformylbenzyloxy)-2-nitropyridine and 3-(2-formyl-6-methylbenzyloxy)-2-nitropyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl alcohol
  6. temperaturecooling
  7. stirringAfter being stirred for 2.5 hours at an ambient temperature
  8. additionthe mixture was diluted with ice water
  9. customThe resulting precipitates
  10. filtrationwere filtrated off
  11. customdried

Sources & evidence

ORD record
ord-21d0fb3680ef4ef491827e18d45e36e0
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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