반응 #988342

반응 방정식

Thionyl chloride

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

diethyl ether

water

→

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

용매

dichloromethane

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   세척washed with conc. sodium bicarbonate solution (10 mL)
3. 3
   건조dried over sodium sulphate
4. 4
   농축concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (5 mL)
6. 6
   기타precipitated by addition of hexane (ca. 50 mL)

실험 절차

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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