Reacción #1605777

Ecuación de reacción

2-hydroxy-4-methyl-benzamide

K2CO3

Me2SO4

→

2-methoxy-4-methyl-benzamide

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   workup.ADDITIONwas added at that temperature
3. 3
   TemperaturaThe resulting mixture was refluxed overnight
4. 4
   FiltraciónThe reaction mixture was then filtered
5. 5
   Concentraciónthe filtrate was concentrated
6. 6
   workup.DISSOLUTIONThe resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1)
7. 7
   OtroAfter removal of the solvent
8. 8
   Otrothe residue was recrystallized from EtOAc/PE

Procedimiento

A mixture of 2-hydroxy-4-methyl-benzamide (15.1 g, 0.1 mol) and K2CO3 (41.7 g, 0.3 mol) in 1000 mL of acetone was heated to reflux for 1 hour before Me2SO4 was added at that temperature. The resulting mixture was refluxed overnight. The reaction mixture was then filtered and the filtrate was concentrated. The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) and stirred at room temperature for 3 hours. After removal of the solvent, the residue was recrystallized from EtOAc/PE to afford 102 g of 2-methoxy-4-methyl-benzamide (yield 61%). 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=7.6 Hz, 1H), 7.57 (br s, 1H), 7.46 (br s, 1H), 6.92 (s, 1 H), 6.81 (d, J=7.6 Hz, 1 H), 3.85 (s, 3H), 2.31 (s, 3H).

Fuente