Acetic Anhydride → 2-(Acetoxymethyl)-4-methoxy-3,5-dimethylpyridine

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Reaction Steps

215 ml of acetic anhydride are added dropwise at room temperature to a solution of 81.5 g of 4-methoxy-2,3,5-trimethylpyridine 1-oxide in 290 ml of chloroform. After boiling under reflux for 4 hours the solution is evaporated, the residue is dissolved in 200 ml of toluene and again evaporated. The residue is taken up in 500 ml of ethyl acetate and shaken out three times with 250 ml of saturated sodium bicarbonate solution. The organic phase is dried over sodium sulphate and evaporated in vacuo. The crude product remaining behind as the residue is chromatographed on 400 g of silica gel with ether. There is obtained (4-methoxy-3,5-dimethyl-2-pyridyl)methyl acetate in the form of an oil.

Provenance & Evidence