Ethanol → (m-Tolyl-hydrazono)-acetic acid

Participants

Reaction Conditions

Reaction Steps

3-Methylphenylhydrazine hydrochloride (15.9 g, 100 mmol) was dissolved in water (450 mL) and ethanol (600 mL) with heating at 60° C. A solution of glyoxylic acid (9.21 g, 100 mmol) in water (100 mL) was added to the warm solution using water (3×15 mL) to rinse. The reaction mixture was stirred at 60° C. for 45 minutes and then cooled slightly and concentrated to remove ethanol. The aqueous mixture was neutralized with NaOH and then water was added (800 mL). The precipitate was filtered, washed with water (3×100 mL), washed with hexanes (100 mL) and dried to give the subtitle compound as a brown solid (12.2 g, 69%).

Provenance & Evidence