Reacción #1256709

Ecuación de reacción

6

4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenol

iodomethane

→

methyl pyridinium iodide salt

4-(4-hydroxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Concentraciónthe mixture was concentrated in vacuo

Procedimiento

To a stirring solution of 6 (0.113 g, 0.500 mmol) in anhydrous methanol (10 mL) was added dropwise iodomethane (0.5 mL, 0.660 g, 2.75 mmol) at room temperature under N2. The reaction mixture was then stirred at 60° C. under N2 overnight. After cooling to room temperature, the mixture was concentrated in vacuo to give the corresponding methyl pyridinium iodide salt as an analytically pure yellow solid (0.184 g, 99.4%). mp 257-258° C.; 1H NMR (500 MHz, DMSO-d6): δ 9.562 (s, 1H), 8.898 (s, 2H), 6.645 (s, 2H), 4.295(s, 3H), 2.015 (s, 6H), 1.760 (s, 6H); 13C NMR (125 MHz, DMSO-d6): δ 157.588, 157.448, 143.158, 136.942, 134.675, 124.179, 114.988, 47.297, 19.162, 16.527; MS (ESI): m/z 242.4 [(M−I)+, 100]; Anal. Calcd. For C16H20INO·H2O: C, 49.62; H, 5.73; N, 3.62; I, 32.77. Found: C, 50.08; H, 5.52; N, 3.65; I, 33.49.

Fuente