Water → 2-(Benzyloxy)-5-(dimethoxymethyl)benzyl alcohol

Participants

Reaction Steps

7 g of lithium aluminum hydride was suspended in 200 ml of tetrahydrofuran under ice-cooling, and 100 ml of tetrahydrofuran solution containing 39.08 g of 2-(benzyloxy)-5-(dimethoxymethyl)benzoic acid methyl ester was added thereto. After stirring for 5 minutes, water, 15% sodium hydroxide and water were added, followed by filtration. The filtrate was evaporated, to give 35.15 g of 2-(benzyloxy)-5-(dimethoxymethyl)benzyl alcohol. This crude product was dissolved in 250 ml of toluene, and 40 g of diphenyl phosphoryl azide and 22 ml of diazabicyclo[5.4.0]undecene were added thereto, and the solution was stirred overnight at room temperature. Water was added to the reaction product, followed by extracting with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 17.4 g of 4-(benzyloxy)-3-(azidomethyl)dimethoxymethylbenzene from fractions eluted with hexane-ethyl acetate (15:1). This product was allowed to stand for 1 month at room temperature, and was purified by silica gel column chromatography, to give 9.39 g of 4-(benzyloxy)-3-(azidomethyl)benzaldehyde from fractions eluted with hexane-ethyl acetate (12:1).

Provenance & Evidence