Benzyl Chloride → Benzyl 2-benzyloxymethyl-4,4-dimethoxybutyl ether

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Reaction Steps

Sodium hydride (55% in oil, 32.72 g, 0.75 mol) was washed twice with n-hexane and suspended in 200 ml of THF. 4,4-Dimethoxy-2-(hydroxymethyl)butanol (49.26 g, 0.3 mol) was added dropwise to maintain a gentle evolution of hydrogen gas. Then benzyl chloride (94.94 g, 0.45 mol) was added during 30 min. and the mixture was refluxed over-night, cooled, diluted with 50 ml of ethanol, and evaporated in vacuum. The residue was suspended in about 200 ml of water and extracted with 3×100 ml of ether. The combined organic extracts were dried (MgSO4) and distilled in vacuum. The title compound (94.34 g, 91%) was obtained at 197°-200° C. (0.01 mm Hg).

Provenance & Evidence