Triethylamine → 3-Benzoylpropionic acid

Participants

Reaction Steps

To a mixture of 24.5 g. 3-(m-toluoyl)propionic acid (0.10 mole) and 10.1 g. triethylamine (0.10 mole) in 250 ml. of chloroform cooled to 0°C., there is added dropwise 10.8 g. (0.10 mole) of ethyl chloroformate at such a rate that the critical temperature does not exceed 10°C. The reaction is stirred for 2 1/2 hours to obtain the mixed anhydride of 3-benzoylpropionic acid which is then treated with 3.1 g. of methylamine (0.10 mole) in 100 ml. of chloroform. The cooling apparatus is removed and the reaction is stirred for about 20 hours. The chloroform layer is then washed with 50 ml. of water, 100 ml. 1N hydrochloric acid, 100 ml. saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue is crystallized from methylene chloride/hexane to give 5-hydroxy-1-methyl-5-(m-tolyl) pyrrolidone; m.p. 128°-130°C.

Provenance & Evidence