Benzene → p-Toluenesulfonic acid

Participants

Reaction Steps

N-isopropyl ethyl glycinate (22.9 g, 0.158 mole) and 33.1 g of p-toluenesulfonic acid monohydrate (0.174 mole) were placed in a reaction vessel filtered with a reflux condenser and a Dean-Stark apparatus. Benzyl alcohol (158 ml, 1.53 mole) and 158 ml of benzene (1.77 mole) were added, and the reaction mixture was refluxed for 24 hours. The reaction mixture was cooled to room temperature, and ~800 ml of ether was added. After stirring at -30° C. overnight, the reaction mixture was filtered and the precipitate collected. The precipitate was washed with cold ether to yield 60.97 g of the impure p-toluenesulfonate salt of the title compound.

Provenance & Evidence