Acetonitrile → 3-(4-Carboxybenzyl)-2,4,5-trimethyloxazolium bromide

Participants

Reaction Steps

2,4,5-Trimethyloxazole (11.66 g), α-bromo-p-toluic acid (21.5 g), and dry acetonitrile (100 ml) were combined and refluxed for 14 hours under nitrogen with constant stirring. Upon cooling to room temperature, the reaction mixture solidified. The solid was diluted with 100 ml acetone and filtered. The collected solid was slurried in 400 ml refluxing acetone for 20 minutes and filtered while hot. The collected solid was again slurried in 400 ml refluxing acetone and filtered while hot. This solid was washed with 100 ml acetone, then 100 ml ligroin P950 and dried to yield 21.6 g 3-(4-carboxybenzyl)-2,4,5-trimethyloxazolium bromide (Intermediate F).

Provenance & Evidence