Sodium Hydroxide → HCID 17964265, compound

Participants

Reaction Steps

Lithium aluminum hydride (0.35 g) was added by small portions over 12 minutes to an ice-cooled solution of (2-methoxyethoxy)methyl 3-[(2-methoxyethoxy)methoxy]-4-methylbenzoate (3.5 g) in tetrahydrofuran (20 ml) below 5° C. under nitrogen atmosphere. After the mixture was stirred at the same temperature for 30 minutes, 2N sodium hydroxide (0.5 ml) was added to the mixture. After the mixture was stirred for 30 minutes, the insoluble materials were removed by filtration and washed with tetrahydrofuran. The filtrate and the washing were combined, and evaporated under reduced pressure. The residue was dissolved into ethyl acetate, and manganese (IV) oxide (3.5 g) was added to the solution. After being stirred under reflux for 2 hours, the reaction mixture was filtered through Celite® and the insoluble mass was washed with ethyl acetate. The filtrate and the washing were combined and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using mixed solvents of hexane and ethyl acetate (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give 3-[(2-methoxyethoxy)methoxy]-4-methylbenzaldehyde (1.7 g) as an oil.

Provenance & Evidence