تفاعل #66917

معادلة التفاعل

H2O

benzyl bromide

68

Ethyl 2-hydroxybenzoate

K2CO3

→

73

المردود 94.7%

Ethyl 2-(benzyloxy)benzoate

المردود 94.7%

المذيبات

CH3CN

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 8 h under N2 atmosphere
2. 2
   درجة الحرارةThe reaction mixture was cooled to 25°
3. 3
   استخلاصextracted with CH2Cl2
4. 4
   غسيلThe organic layer was washed with H2O
5. 5
   تجفيفdried over MgSO4
6. 6
   أخرىevaporated
7. 7
   workup.DISTILLATIONThe crude products were purified by distillation

الإجراء التجريبي

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.

المصدر