Introduction Vanillin is a phenolic aldehyde with the molecular formula C8H8O3. Thus, it has three t — Organic Chemistry Chemistry Question

Introduction
Vanillin is a phenolic aldehyde with the molecular formula C₈H₈O₃. Thus, it has three types of functional groups including aldehyde, ether, and phenol. This compound is often used as a flavoring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanilla planifolia. It is known that the aldehyde functional group in vanillin can be easily converted into enamine derivatives or imides through the condensation reaction between vanillin and amines. The products are synthones which are widely applied in the synthetic organic chemistry and pharmaceuticals.

Chemicals and Reagents
* Vanillin: 1-2 g
* Benzylamine
* Dichloromethane: 20 cm₃
* Sodium sulfate, Na₂SO₄

Equipment and Glassware
* Erlenmeyer flasks, 250 cm₃
* Graduated cylinders, 10, 25, 50 cm₃
* Beral pipets
* Beakers, 50 cm₃
* Hot plate
* Spatulas
* Büchner funnel with filter flask and filter paper, separating funnel
* Melting point apparatus and capillary tubes
* Small vials with caps
* Vials with caps, 20 cm₃
* Thin layered chromatography (TLC) spotters
* TLC plates (silica with fluorescent indicator A254)
* Chamber for TLC development
* Magnetic stirrer,Ice water bath

Experimental procedure
1. Add 1.0 g of vanillin into a dry 50 cm₃ flask then add 10 cm₃ of dichloromethane solvent into the flask. The mixture is stirred for 10 min at room temperature, and then 0.7 g of benzylamine and 2.0 g of Na₂SO₄ are simultaneously added into the flask.
2. The reaction mixture is further stirred at reflux condition (65 – 67 oC) for 90 min. Cool the flask to room temperature.
3. Dilute the resultant mixture with 40 cm₃ and swirl the flask.
4. Transfer the mixture into a separating funnel and then extract with 30 cm₃ of dichloromethane. Extract the organic phase 2 times more with 30 cm₃ of dichloromethane.
5. Dry the extracting organic fraction with MgSO₄. Filter the organic fraction through a Buchner funnel. Discard the solid and collect the filtrate.
6. Remove the solvent in the filtrate by rotary evaporation to obtain the product(s).
7. Determine the purity of the crude product by thin layer chromatography method. Use precoated silica gel plates (Silica Gel PF^-254) and visualize the spots by UV-light. Use ethyl acetate: heptane 15:85 mixture as an eluent.
Note: It is recommended to carry out the experiment under a hood.