Part 2: Etherification of Intermediate Product

Transfer 0.1 g of 'wet' Amberlyst into a small round bottom flask, and wash three times with 1 mL portions of methanol, removing the methanol each time with a pipette, then add 2 mL of fresh methanol and a stir bar to the round bottom flask. Next, add 0.10 g of the product from part 1, and remove 1 drop to spot to a TLC plate.

Place a condenser on the reaction flask, and heat to reflux for 15 minutes.

Lift the reaction flask out of the sand bath, remove one drop of the reaction, and spot to the TLC plate. Run the TLC plate to check for reaction completion, if the reaction has not finished, reflux for 15 additional minutes. If the reaction was completed, add 0.050 g of sodium bicarbonate and stir for 5 more minutes.

Filter out the Amberlyst using a pasteur pipette with a glass fiber plug, and transfer the remaining liquid to a small Erlenmeyer flask. Place your flask in the sand bath, and evaporate the solvent.

Your product (methyl diantilis) may form either a liquid or a solid. In either case, you will need to weigh your final product, and prepare an NMR sample using ~40 mg of methyl diantilis and 0.7 mL of DMSO-d6.