反応 #66917

反応方程式

H2O

benzyl bromide

68

Ethyl 2-hydroxybenzoate

K2CO3

→

73

収率 94.7%

Ethyl 2-(benzyloxy)benzoate

収率 94.7%

溶媒

CH3CN

反応条件

後処理

1. 1
   温度refluxed for 8 h under N2 atmosphere
2. 2
   温度The reaction mixture was cooled to 25°
3. 3
   抽出extracted with CH2Cl2
4. 4
   洗浄The organic layer was washed with H2O
5. 5
   乾燥dried over MgSO4
6. 6
   その他evaporated
7. 7
   workup.DISTILLATIONThe crude products were purified by distillation

実験手順

To a solution of 68 (5.8 g, 34.9 mmol) in CH3CN (150 ml) was added K2CO3 (10.6 g, 76.8 mmol). The mixture was added benzyl bromide (6.57 g, 38.39 mmol) and refluxed for 8 h under N2 atmosphere. The reaction mixture was cooled to 25° and poured into H2O (500 ml), and then extracted with CH2Cl2. The organic layer was washed with H2O, dried over MgSO4 and evaporated. The crude products were purified by distillation to give 73 as colorless liquid. (8.5 g, 33.2 mmol). Yield: 94.71%; MS (EI, 70 eV): m/z 256.3 (M+); 1H-NMR (CDCl3, 200 MHz): δ 1.33=(t, J=7.2 Hz, 3H), 4.35 (q, =7.2, 7.0 Hz, 2H), 5.15 (s, 2H), 7.00 (d, =8.0 Hz, 2H), 7.32-7.45 (m, 5H), 7.49 (d, J=8.2 Hz, 1H), 7.82 (dd, J=8.2, 1.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 166.60, 158.01, 136.77, 133.25, 131.69, 128.49, 127.80, 126.99, 121.20, 120.56, 113.75, 70.57, 60.93, 14.29; Anal. Calcd for C16H16O3: C, 74.98; H, 6.29.

出典