Reaction #2146678

ord-948ec4c531f544f18e56154f9bc23a32

Reaction equation

CC(=O)c1ccncc1
4-Acetylpyridine
COS(=O)(=O)c1ccc(C)cc1
p-toluene sulfonic acid methyl ester
→
CC(=O)c1cc[n+](C)cc1.Cc1ccc(S(=O)(=O)[O-])cc1
4-acetyl-1-methylpyridinium p-toluene sulfonate

Reactants

CC(=O)c1ccncc1
4-Acetylpyridine
COS(=O)(=O)c1ccc(C)cc1
p-toluene sulfonic acid methyl ester

Reagents

None

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureunder reflux for 5 hours
  2. 2
    OtherThe solvent was removed under vacuum in a rotary evaporator
  3. 3
    OtherAfter separating off the ether phase
  4. 4
    Otherthe product slowly crystallized out
  5. 5
    OtherThe product was dried under vacuum

Procedure

4-Acetylpyridine (30.0 g, 0.25 mol) and p-toluene sulfonic acid methyl ester (55.8 g, 0.30 mol) in 500 ml ethanol were heated under reflux for 5 hours. The solvent was removed under vacuum in a rotary evaporator and the residue was taken up in ether. After separating off the ether phase, the product slowly crystallized out. The product was dried under vacuum. Yield: 59.9 g (82.5%);

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08277516B2uspto-grants-2012_10