Hydrogen Peroxide → Methyl 4-(hydroxymethyl)-2-methylbenzoate

Participants

Reaction Steps

1.70 g of 4-(methoxymethoxymethyl)-2-methylbenzaldehyde was dissolved in 10 mL of acetonitrile, to which 3.69 g of sodium dihydrogen phosphate dihydrate dissolved in 7 mL of water and 1.58 g of a 80% sodium chlorite dissolved in 3 mL of water and a 1.5 mL of 30% aqueous solution of hydrogen peroxide were successively added at 5 to 10° C., and then this solution was stirred for 20 minutes at room temperature. Then, ethyl acetate and water were added to the reaction mixture, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was dissolved in 18 mL of methanol, to which 9 mL of 6M hydrochloric acid was added, and this mixture was stirred for 4.5 hours while heating it under reflux. The reaction mixture was cooled to room temperature, and poured into a mixture of chloroform and water, then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:1] to yield 1.30 g of methyl 4-(hydroxymethyl)-2-methylbenzoate as light yellow oil.

Provenance & Evidence