Réaction #66917

Équation de réaction

H2O

benzyl bromide

68

Ethyl 2-hydroxybenzoate

K2CO3

→

73

Rendement 94.7%

Ethyl 2-(benzyloxy)benzoate

Rendement 94.7%

Solvants

CH3CN

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 8 h under N2 atmosphere
2. 2
   TempératureThe reaction mixture was cooled to 25°
3. 3
   Extractionextracted with CH2Cl2
4. 4
   LavageThe organic layer was washed with H2O
5. 5
   Séchagedried over MgSO4
6. 6
   Autreevaporated
7. 7
   workup.DISTILLATIONThe crude products were purified by distillation

Mode opératoire

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.

Source