反応 #1605777

反応方程式

2-hydroxy-4-methyl-benzamide

K2CO3

Me2SO4

→

2-methoxy-4-methyl-benzamide

溶媒

acetone

反応条件

後処理

1. 1
   温度was heated
2. 2
   workup.ADDITIONwas added at that temperature
3. 3
   温度The resulting mixture was refluxed overnight
4. 4
   ろ過The reaction mixture was then filtered
5. 5
   濃縮the filtrate was concentrated
6. 6
   workup.DISSOLUTIONThe resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1)
7. 7
   その他After removal of the solvent
8. 8
   その他the residue was recrystallized from EtOAc/PE

実験手順

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).

出典