Hydrochloric Acid → 4-Acetamido-3-(2-hydroxyethoxy)benzoic acid

Participants

Reaction Steps

A sample of methyl 4-acetylamino-3-(2-hydroxyethoxy)benzoate (1.51 g, 0.0060 mol) was suspended in 1N NaOH (12.0 mL, 0.0119 mol). After stirring for 1 h, thin-layer chromatographic analysis (SiO2, ethyl acetate) showed disappearance of starting material along with appearance of a new lower-running spot (Rf =0.1) indicating the reaction was complete. The reaction mixture when neutralized with concentrated HCl formed a white precipitate. The material was collected by filtration, washed with water, and then dried in vacuo at acetone reflux to give 0.47 g (34%) of the title compound as a tan solid, mp 207.5°-208.5° C.

Provenance & Evidence