Part 1: Reduction of Ethylvanillin

Place a stir bar, the ethyl vanillin, and NaOH in a 25 mL Erlenmeyer flask. Cool the flask in an ice-bath, and add 0.075 g of sodium borohydride in small amounts.

Remove the flask from the ice bath and allow it to come to room temperature then allow fifteen minutes for the reaction to proceed.

Cool the reaction flask again by placing it in an ice bath, then slowly add 2.5 M HCL 1 mL at a time until the pH becomes acidic. Then allow the flask to stir for an additional 5 minutes.

Vacuum filter the precipitate, washing the flask, and then further washing the crystals with three 2 mL portions of cold water. Then allow the solid to dry for 15 minutes under vacuum. Remove the crystals from the filter paper, and weigh the intermediate product.

Run a TLC of the intermediate product compared to ethyl vanillin using 1:1 hexane:ethyl acetate. Prepare an NMR sample using ~40 mg of the intermediate product and 0.7 mL of DMSO-d6.

Note: Two mistakes were made in the video above. What are they? Discuss with your partners!