Water → 3-(Hydroxymethyl)-5-(methoxymethoxy)phenol

Participants

Reaction Steps

With ice cooling, to a solution of aluminum lithium hydride (1.80 g, 47.5 mmol) in tetrahydrofuran (50 mL) was added dropwise a solution of methyl 3-hydroxy-5-(methoxymethoxy)benzoate (7.74 g, 36.5 mmol) in tetrahydrofuran (50 mL), and the mixture was stirred at room temperature for 4 hours. To the reaction solution were successively added water (2 mL), a 15% aqueous sodium hydroxide solution (2 mL) and water (7 mL), and the mixture was further stirred for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5) to give the title compound (4.46 g, yield 66%) as an oily matter.

Provenance & Evidence