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

Participants

Reaction Steps

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.

Provenance & Evidence