Chloromethyl Methyl Ether → HCID 68194700, compound

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Reaction Steps

[4-(4-Bromobenzyl)phenyl]methanol (2.7 g, 9.6 mmol) was dissolved in tetrahydrofuran (50 mL), and sodium hydride (55%, 0.50 g, 12 mmol) was added at 0° C., followed by stirring at the same temperature for 30 minutes under a nitrogen atmosphere. To the reaction solution at 0° C. was added dropwise a solution of chloromethyl methyl ether (1.0 g, 13 mmol) in tetrahydrofuran (10 mL), followed by stirring at room temperature for 4 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.55 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (2.5 g, 7.8 mmol) as a colorless oil (yield 81%).

Provenance & Evidence