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

HRID 909950Notes

Reaction equation

HRID 909950 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. Yield: 59.9 g (82.5%); 1H-NMR (400 MHz, DMSO-d6): [delta] [ppm]=2.26 (s, 3H); 2.72 (s, 3H); 3.39 (s, 3H); 7.11 (d, 2H); 7.49 (d, 2H); 8.42 (d, 2H); 9.20 (d, 2H); 13C-NMR (400 MHz, DMSO-d6): [delta] [ppm]=20.8; 26.4; 48.1; 124.8; 125.3; 127.7; 138.9; 145.2; 146.5; 148.3; 195.8.

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-3b6e174cd37246e7a98339b4cf85d789
Source dataset
uspto-grants-2011_09
Patent number
US08021438B2

Reaction notes

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