video tutorial Make nitrovanillin via nitration of vanillin

Name: video tutorial - Make nitrovanillin via nitration of vanillin
Uploaded: 2025-12-11T09:03:43.761Z
Duration: 12 min 2 s
Description: we'd have a go at making one up. Vanillin is a phenol, so the aromatic ring is pretty activated...towards electrophilic attack. So nitration should be pretty easy. With phenol for instance dilute

Goal: explore nitration of vanillin to 5-nitrovanillin; initial attempts with dilute nitric acid led to vigorous reaction, so a controlled method was developed.
Solvent and setup: vanillin (25 g) dissolved in dichloromethane (≈130 mL total) with cooling to keep reaction exothermic under control; nitric acid (68%, ~16–17 mL used) added dropwise; reaction produced a yellow color and red aqueous phase, with gentle bubbling if acid was added too quickly.
Workup and product: after reaction, mixture cooled and water added; yellow solid filtered, washed with cold water to pale yellow filtrate; dried solid weighed about 36 g (weight gain from nitration).
Purification: crude product recrystallized from hot ethanol (also tested acetone); 10 g of crude yielded ~2.4 g of purified crystals; ethanol (and acetone) were not ideal recrystallization solvents; chloroform not available but considered for future work.
Characterization: purified crystals tested by melting behavior; initial melting observed around 162–170°C, with literature value for 5-nitrovanillin near 175°C; results consistent with 5-nitrovanillin; burning test indicated a stable, non-explosive solid.
Yield and outlook: about 5–6 g of product obtained across attempts; remaining product largely in ethanol filtrate, indicating solvent inefficiency for purification; plan to optimize recrystallization solvent and continue experiments after vacation.