Water → 4-(Ethoxymethyl)benzenemethanol

Participants

Reaction Steps

Lithium aluminum hydride (0.39 g) was suspended in tetrahydrofuran (10 mL), a solution of 4-(ethoxymethyl)benzoic acid methyl ester (2.0 g) synthesized in Reference Example 38 in tetrahydrofuran (50 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was ice-cooled, and water (1.0 mL) and aqueous sodium hydroxide solution (1 mol/L, 4.0 mL) were successively added dropwise. After warming to room temperature, the mixture was stirred for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (1.52 g) as a colorless oil.

Provenance & Evidence