Реакция #1605777

Уравнение реакции

2-hydroxy-4-methyl-benzamide

K2CO3

Me2SO4

→

2-methoxy-4-methyl-benzamide

Растворители

acetone

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   workup.ADDITIONwas added at that temperature
3. 3
   ТемператураThe resulting mixture was refluxed overnight
4. 4
   ФильтрацияThe reaction mixture was then filtered
5. 5
   Концентрированиеthe filtrate was concentrated
6. 6
   workup.DISSOLUTIONThe resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1)
7. 7
   ДругоеAfter removal of the solvent
8. 8
   Другоеthe residue was recrystallized from EtOAc/PE

Методика

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).

Источник