Реакция #48207

Уравнение реакции

Thionyl chloride

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

diethyl ether

water

→

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

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеThe organic layer was separated
2. 2
   Промывкаwashed with conc. sodium bicarbonate solution (10 mL)
3. 3
   Сушкаdried over sodium sulphate
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (5 mL)
6. 6
   Другоеprecipitated by addition of hexane (ca. 50 mL)

Методика

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]+).

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