Benzyl Alcohol → (S)-N-Methylalanine benzyl ester p-toluene sulfonic acid salt

Participants

Reaction Steps

A suspension of 1.55 g (15.0 mmol) of (S)-N-methylalanine and 9.31 (90.0 mmol) of benzyl alcohol in 30 mL of toluene was treated with 3.00 g (15.8 mmol) of p-toluenesulfonic acid monohydrate. The mixture was heated for 19 hours under reflux with removal of water via a Dean-Stark trap. After cooling, the reaction solution was poured into 200 mL of ether, precipitating a yellow oil. The solvents were decanted and the residue was taken up into ethyl acetate and concentrated to yield a viscous, light yellow oil (22); TLC: Rf =0.34, 95:5:0.5 CH2Cl2 /MeOH/concentrated ammonium hydroxide; 1H NMR (300 MHz) consistent with structure.

Provenance & Evidence