Acetic Acid → 3,5-Dimethylpyridin-1-ium-1-olate

HRID 974083Notes

Reaction equation

HRID 974083 reaction equation
C(O)(=[O:3])C.[CH3:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([CH3:12])[CH:11]=1.C(OO)(=O)C.[O-]S([O-])=O.[Na+].[Na+]>O>[CH3:5][C:6]1[CH:7]=[N+:8]([O-:3])[CH:9]=[C:10]([CH3:12])[CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6585Peracetic Acid2×HCID 115653,5-DimethylpyridineHCID 24437Sodium Sulfite

Product 1

HCID 194853,5-Dimethylpyridin-1-ium-1-olate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

98 ml of glacial acetic acid were added dropwise, at 25° C., to 350 g of 3,5-dimethylpyridine. The mixture was heated to 50° C. and 870.3 g of 40% peracetic acid were metered in such that the temperature could be kept at 50° C. by cooling. About 1 hour after the addition of the peracetic acid had ended, the reaction mixture was cooled to 25° C. and 230 g of Na2SO3 in 1 1 of water were added dropwise, with cooling. After the excess peracetic acid had been destroyed (KI-starch test), 1330 ml of water were added, the mixture was rendered alkaline with 730 ml of 50% NaOH and the solution was extracted in several portions with a total of about 4500 ml of chloroform. The combined organic phases were dried with Na2SO4 and the solvent was evaporated off to about 740 ml.

Workup

  1. customcould be kept at 50° C.
  2. temperatureby cooling
  3. temperaturethe reaction mixture was cooled to 25° C.
  4. temperaturewith cooling
  5. customAfter the excess peracetic acid had been destroyed (KI-starch test), 1330 ml of water
  6. additionwere added
  7. extractionthe solution was extracted in several portions with a total of about 4500 ml of chloroform
  8. dry with materialThe combined organic phases were dried with Na2SO4
  9. customthe solvent was evaporated off to about 740 ml

Sources & evidence

ORD record
ord-54c47f6a14fc446cbeaf20dbd74221be
Source dataset
uspto-grants-1991_11
Patent number
US05066810

Reaction notes

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