反应 #48207

反应方程式

Thionyl chloride

(4-benzyloxy-3-chloro-5-methoxy-phenyl)-methanol

diethyl ether

water

→

2-Benzyloxy-1-chloro-5-chloromethyl-3-methoxy-benzene

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他The organic layer was separated
2. 2
   洗涤washed with conc. sodium bicarbonate solution (10 mL)
3. 3
   干燥dried over sodium sulphate
4. 4
   浓缩concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (5 mL)
6. 6
   其他precipitated by addition of hexane (ca. 50 mL)

实验过程

Thionyl chloride (2 mL) was added to solution of (4-benzyloxy-3-chloro-5-methoxy-phenyl)-methanol (CAB02170, 2.703 g, 9.7 mmol) in dichloromethane (10 mL). The solution was stirred for 1 h at room temperature, then diethyl ether (50 mL) and water (20 mL) were added. The organic layer was separated, washed with conc. sodium bicarbonate solution (10 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in dichloromethane (5 mL) and precipitated by addition of hexane (ca. 50 mL). Yield: 2.730 g (95%) white powder. 1H-NMR (400 MHz, CDCl3) δ=3.89 (s, 3H, —OCH3), 4.52 (s, 2H), 5.07 (s, 2H), 6.87 (d, J=2.0 Hz, 1H), 7.03 (d, J=2.0 Hz, 1H), 7.33-7.43 (m, 3H), 7.53-7.58 (m, 2H). LRMS (FAB+): 91.0 (100), 296.0 (17, [M+H]+).

来源