Potassium Carbonate → 4-Acetylamino-2-hexyloxybenzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of p-acetylaminosalicylic acid methyl ester (5.0 g), hexyl iodide (7.6 g), potassium carbonate (9.9 g), and dimethylformamide (20 ml) is stirred at 70° C. for 30 hours. The reaction mixture is poured into ice-water and extracted with diethyl ether. The organic layer is washed successively with aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated. The residue is chromatographed on silica gel with chloroform-methanol (20:1) to give 4-acetylamino-2-hexyloxybenzoic acid methyl ester (4.9 g) as an oil.

Provenance & Evidence