Benzyl Alcohol → L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

Participants

Reaction Steps

In a 200 ml 3 neck flask equipped with a Dean and Stark trap, reflux condenser (with drying tube attached), and mechanical stirrer, 15 grams (0.0789 mole) of p-toluenesulfonic acid monohydrate is refluxed until one equivalent of water is released. At this point 10 grams (0.07634 mole) leucine and 17.0 grams (0.15 mole) benzyl alcohol are added. The mixture is refluxed for 4 hours and allowed to cool to room temperature. The solvents are removed in vacuo and a white, solid residue is produced. The white solid is washed with anhydrous ether and recrystallized from ethanol/ether to yield in three crops 28.2 grams of leucine benzyl ester p-toluene sulfonate (94% yield) having a melting point of 157°-158° C. (with decomposition).

Provenance & Evidence