Sulfuric Acid → Methyl 4-(4-aminophenyl)-4-oxobutanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 35 g. of 3-(4-acetamidobenzoyl)propionic acid, 700 ml. of methanol and 1.4 ml. of concentrated sulfuric acid is refluxed for 76 hours. The solution is cooled to 35° C. and poured onto 7 g. of anhydrous sodium acetate while stirring. The reaction mixture is stirred in an ice-bath. The solid is collected and washed with cold methanol to yield methyl 3-(4-aminobenzoyl)propionate as a white solid. A mixture of this solid, 8.0 g. of 14-(trimethylsilyl)tetradecyl bromide and 4.2 g. of potassium carbonate is stirred for 20 hours at 125° C. under nitrogen. The mixture is then cooled to 25° C. and 30 ml. of water is added. After stirring, the product is filtered and washed with water. Recrystallization affords methyl 3-[4-[14-(trimethylsilyl)tetradecylamino]benzoyl]propionate as a white solid.

Provenance & Evidence