반응 #66917

반응 방정식

H2O

benzyl bromide

68

Ethyl 2-hydroxybenzoate

K2CO3

→

73

수율 94.7%

Ethyl 2-(benzyloxy)benzoate

수율 94.7%

용매

CH3CN

반응 조건

후처리

1. 1
   온도refluxed for 8 h under N2 atmosphere
2. 2
   온도The reaction mixture was cooled to 25°
3. 3
   추출extracted with CH2Cl2
4. 4
   세척The organic layer was washed with H2O
5. 5
   건조dried over MgSO4
6. 6
   기타evaporated
7. 7
   workup.DISTILLATIONThe crude products were purified by distillation

실험 절차

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.

출처