Methyl p-toluenesulfonate → Pyridinium, 4-acetyl-1-methyl-, 4-methylbenzenesulfonate (1:1)

HRID 2059497Notes

Reaction equation

HRID 2059497 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:10][O:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>C(O)C>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([S:12]([O-:14])(=[O:11])=[O:13])=[CH:20][CH:19]=1.[C:1]([C:4]1[CH:9]=[CH:8][N+:7]([CH3:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 142824-Acetylpyridine

Product 1

HCID 53250141Pyridinium, 4-acetyl-1-methyl-, 4-methylbenzenesulfonate (1:1)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solvent was removed under vacuum in a rotary evaporator
  3. customAfter separating off the ether phase
  4. customthe product slowly crystallized out
  5. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-8b3bc44f5cf34c75830b17b4c56ae364
Source dataset
uspto-grants-2012_10
Patent number
US08277517B2

Reaction notes

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